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[ CAS No. 720-44-5 ] {[proInfo.proName]}

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Chemical Structure| 720-44-5
Chemical Structure| 720-44-5
Structure of 720-44-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 720-44-5 ]

CAS No. :720-44-5 MDL No. :MFCD00014398
Formula : C14H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BEGZWXVLBIZFKQ-UHFFFAOYSA-N
M.W : 214.26 Pubchem ID :95375
Synonyms :

Calculated chemistry of [ 720-44-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.55
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 2.95
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.38
Solubility : 0.0885 mg/ml ; 0.000413 mol/l
Class : Soluble
Log S (Ali) : -3.23
Solubility : 0.126 mg/ml ; 0.000587 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.52
Solubility : 0.00644 mg/ml ; 0.0000301 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 720-44-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P332+P313-P391-P501 UN#:3077
Hazard Statements:H302+H312-H315-H318-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 720-44-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 720-44-5 ]

[ 720-44-5 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 611-94-9 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydridoborate In methanol for 1.5h;
99% With sodium tetrahydridoborate In methanol 1 p-methoxybenzhydryl alcohol p-methoxybenzhydryl alcohol Solid NaBH4 (2.55 g, 0.067 mol) was added portion-wise to a solution of p-methoxybenzophenone (25.14 g, 0.118 mol) in MeOH (150 mL) at room temperature over 10 min. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 2 h. TLC (SiO2, CHCl3) indicated incomplete reaction; therefore, additional NaBH4 (2.55 g) was added and the reaction mixture was stirred at room temperature an additional 2 h. The MeOH was evaporated and the residue partitioned between water (100 mL) and CH2 Cl2 (100 mL). The layers were separated, and the aqueous layer was extracted with CH2 Cl2 (200 mL). The combined organic layers were dried (Na2 SO4), filtered and evaporated to give the alcohol (25.24 g, 99%) as a white solid: m.p. 66-67° C. The structure was confirmed by 1 H--NMR in CDCl3.
99% With sodium tetrahydridoborate In methanol at 20℃; for 2h;
98% With ammonia hydrochloride; aluminium In ammonia at 25℃; for 4h; Irradiation;
98% With [(OC-6-13)-RuCl2[P(p-CH3C6H5)3]2(en)]; potassium-t-butoxide; hydrogen In isopropanol at 35℃; for 18h;
97% With mesoporous silica; sodium cyanotrihydridoborate at 70 - 80℃; for 3.8h; Neat (no solvent); regioselective reaction;
96% With Zn(2+)*2BH4(1-)*C6H7NO In acetonitrile at 20℃; for 2h; chemoselective reaction; Reduction of Benzaldehyde to Benzyl alcoholwith [Zn(BH4)2(2-MeOpy)] General procedure: A Typical ProcedureIn a round-bottomed flask (10 mL),equipped with a magnetic stirrer, a solution ofbanzaldehye (0.106 g, l mmol) in CH3CN (3 mL)was prepared. The complex reducing agent (0.1 g,0.5 mmol) was then added and the mixture wasstirred at room temperature. TLC monitored theprogress of the reaction (eluent; Hexane/EtOAc: 9/1). After completion of the reaction within 1 min, asolution of 5% HCl (5 mL) was added to the reactionmixture and stirred for 5 min. The mixture was extracted with CH2Cl2 (3 × 10 mL) and dried overthe anhydrous sodium sulfate. Evaporation of thesolvent and short column chromatography of theresulting crude material over silica gel (0.015-0.040mm) by eluent of (Hexane/EtOAc: 9/1) afforded thepure liquid benzyl alcohol (0.105 g, 98% yield)
95% With ammonium sulphate; sodium tetrahydridoborate In tetrahydrofuran; water monomer at 20℃; for 2h; A typical procedure for reduction of ketones with the NaBH4/(NH4)2SO4 system in wet-THF General procedure: In a round-bottomed flask (10 mL)equipped with a magnetic stirrer and a condenser,a solution of acetophenone (0.12 g, l mmol) in THF-H2O (3:0.6 mL) was prepared and NaBH4(0.038 g,1 mmol) and (NH4)2SO4(0.234 g, 2 mmol) wereadded and the mixture was stirred at roomtemperature for 90 minutes. TLC monitored theprogress of the reaction (Hexane/EtOAc: 9/1). Aftercompletion of the reaction distilled water (5 mL)was added to the reaction mixture and it was stirredfor an additional 1 minute. The mixture wasextracted with CH2Cl2(3×10 mL) and dried overanhydrous sodium sulfate. Evaporation of thesolvent and short column chromatography of theresulting crude material over sil-ica gel (Hexane/EtOAc: 9/1) afforded the pure crystals of 1-phenylethanol (0.l1 g, 96% yield, Table 1, entry 8).
94% With sodium tetrahydridoborate; pyrographite In tetrahydrofuran; water monomer at 20℃; for 0.333333h;
94% With sodium tetrahydridoborate; diammonium oxalate In acetonitrile for 1.33333h; Reflux;
94% With zinc(II) tetrahydroborate In tetrahydrofuran; water monomer at 20℃; for 4h;
94% With methanol; sodium tetrahydridoborate at 0℃; for 0.166667h;
93% With (4-NHCpr)Triaz(NHP<SUP>i</SUP>Pr<SUB>2</SUB>)<SUB>2</SUB>Mn(CO)<SUB>2</SUB>Br; potassium-t-butoxide; hydrogen In toluene at 80℃; for 4h; Inert atmosphere; Autoclave;
93% With lithium tert-butylate In isopropanol at 20℃; for 24h; UV-irradiation;
91% Stage #1: 4-Methoxybenzophenone With triethylsilane; 9-BBN-2,6-lutidine borenium bistriflimide In dichloromethane at 20℃; Glovebox; Inert atmosphere; Sealed tube; Stage #2: With ferric(III) chloride In methanol at 20℃;
91% With C37H30Cl2N3OPRu; sodium isopropanolate; isopropanol for 0.333333h; Reflux;
90% Stage #1: 4-Methoxybenzophenone With ferrous acetate; tricyclohexylphosphine In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: In tetrahydrofuran at 65℃; for 16h; Inert atmosphere; Stage #3: With water monomer; sodium hydroxide In tetrahydrofuran; methanol at 0 - 20℃; Inert atmosphere;
90% With C21H19ClN3RuS(1+)*F6P(1-); isopropanol; potassium hydroxide at 80℃; for 3h;
90% With aluminum(III) oxide; zinc(II) tetrahydroborate In tetrahydrofuran at 20℃; for 4h; chemoselective reaction; A typical procedure for reduction of ketones to alcohols with the Zn(BH4)2/Al2O3 system in THF General procedure: In a round-bottomed flask (10 mL) equipped with a magnetic stirrer, a solution ofacetophenone (0.121 g, 1 mmol) in THF (3 mL) was prepared. To this solution, Zn(BH4)2(0.095 g, 1 mmol) and then neutral Al2O3 (0.101 g, 1 mmol) were added. The resulting mixturewas stirred at room temperature for 60 min. The progress of the reaction was monitoredby TLC (eluent, CCl4/Et2O: 5/2). After completion of the reaction, distilled water (1 mL) wasadded to the reaction mixture and then stirring was continued for an additional 5 min. Themixture was extracted with CH2Cl2 (3×8 mL) and dried over anhydrous sodium sulfate. Evaporationof the solvent and short column chromatography of the resulting crude material overabove mentioned silica gel afforded pure crystals of 1-phenylethanol (0.11 g, 93 % yield,Table IV, entry 2)
89% With nickel oxide; aluminum(III) oxide; potassium hydroxide; isopropanol In nitrobenzene for 1h; Heating;
88% Stage #1: 4-Methoxybenzophenone With bis(η5-cyclopentadienyl) titanium dichloride; sodium tetrahydridoborate In 1,2-dimethoxyethane at 20℃; Stage #2: With sodium hydroxide In 1,2-dimethoxyethane
82% With potassium hydroxide In isopropanol at 90℃; for 18h; Schlenk technique; Sealed tube;
81% With ammonia; lithium perchlorate In N,N-dimethyl-formamide at 20℃; Electrochemical reaction;
80% With zinc(II) tetrahydroborate In water monomer for 0.0333333h; Microwave irradiation; Green chemistry; Reduction of benzaldehydewith Zn(BH4)2/Microwave Irradiation, A typical procedure General procedure: Zn(BH4)2was prepared from ZnCl4 (5.452g, 0.04 mol) and NaBH4(3.177 g, 0.084 mol)according to an available procedure in the literature11.In a round-bottomed flask (10 mL) charged withdistilled water (5 mL), Zn(BH4)2(0.095 g, 1mmol)and benzaldehyde (0.106 g, 1 mmol) was added.After fitting the flask to the external condenser atthe inside of the oven, the mixture was irradiatedwitha microwave oven (30% power amplitude, 300 W)for60 sec. The progress of the reaction wasmonitored by TLC(eluent; CH2Cl2). At the end of thereduction, distilledwater (5 mL) was added to thereaction mixture and it wasthen extracted withCH2Cl2(2×10 mL). The combined extracts were dried over anhydrous sodium sulfate. Evaporationofthe solvent afforded the pure liquid benzyl alcohol(0.102 g, 95%).
79% With sodium tetrahydridoborate In 1,4-dioxane; water monomer for 24h; Ambient temperature;
71% With sodium hydroxide; aluminium In methanol for 3h;
70% With potassium hydroxide; isopropanol for 5h; Heating;
69% With C19H29N4Ru(1+)*C24H20B(1-); potassium hydroxide In isopropanol at 80℃; for 2h; Inert atmosphere; Schlenk technique;
62% With lithium iodide In N,N-dimethyl-formamide controlled potential electrolysis at -1.80 V vs. SCE;
61% With methanol; C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Sealed tube; Inert atmosphere;
43% Stage #1: 4-Methoxybenzophenone With acetic acid In acetonitrile at 25℃; for 0.0833333h; Stage #2: In acetonitrile at 25℃; for 12h; Electrochemical reaction;
With sodium mercury amalgam; ethanol
With ethanol; aluminum amalgam
With sodium hydroxide; zinc powder
With tris isopropylate aluminium; isopropanol (+-)-4-methoxy-benzhydrol;
With sodium isopropanolate; isopropanol Einwirkung von Sonnenlicht; (+-)-4-methoxy-benzhydrol;
With lithium aluminium hydride
With sodium hydroxide; zinc powder
With sodium tetrahydridoborate In isopropanol
With TEA In methanol for 6h; Irradiation;
With potassium hydroxide; zinc powder In ethanol
With sodium tetrahydridoborate In methanol Ambient temperature;
With lithium aluminium hydride In diethyl ether Heating;
With sodium tetrahydridoborate In ethanol
5 g With sodium tetrahydridoborate In ethanol
With sodium tetrahydridoborate Hydrogenation;
With nickel Hydrogenation;
With sodium tetrahydridoborate
With sodium tetrahydridoborate In methanol
With sodium tetrahydridoborate In methanol at 40 - 50℃;
With sodium tetrahydridoborate In methanol
With sodium tetrahydridoborate
With sodium tetrahydridoborate In methanol
With sodium tetrahydridoborate In ethanol
With sodium tetrahydridoborate In methanol
87 %Chromat. With bis(acetonitrile)bis(2,4-pentanedionato)ruthenium(II); isopropanol; sodium hydroxide at 80℃; for 12h;
73 %Chromat. With sodium hydroxide In isopropanol at 82℃; for 0.75h; 2.3. Transfer hydrogenation of carbonyl compounds General procedure: In a typical procedure, a 5 mg (0.77 mol%) of RuO2/MWCNT and 80 mg (2 mmol) of NaOH were stirred with 5 mL of i-PrOH taken in an ace pressure tube equipped with a stirring bar. Then the substrate (1 mmol) was added to the stirring solution and then the mixture was heated at 82°C. The completion of the reaction was monitored by GC. After the reaction, the catalyst was separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was alsocalculated. Finally, the separated RuO2/MWCNT was washed well with diethyl ether followed by drying in an oven at 60°C for 5 h and it was reused for the subsequent transfer hydrogenation of carbonyl compounds to investigate the reusability of the RuO2/MWCNT.
With sodium tetrahydridoborate In methanol
97 %Chromat. With C16H33Cl2CoN5P2; hydrogen; sodium tertiary butoxide In tert-Amyl alcohol at 20℃; for 24h; Autoclave;
With sodium tetrahydridoborate In methanol
66 %Chromat. With C31H32ClN3ORu; isopropanol; sodium hydroxide for 24h; Reflux; Inert atmosphere;
With sodium tetrahydridoborate In methanol at 0 - 25℃; for 2h; Inert atmosphere;
With sodium tetrahydridoborate
Multi-step reaction with 2 steps 1: lithium triethylhydroborate / tetrahydrofuran / 0.5 h / 20 °C 2: sodium hydroxide / tetrahydrofuran; diethyl ether; water monomer / 0.5 h / 20 °C
With tripotassium phosphate tribasic; 1-(4-(dimethylamino)phenyl)ethyl alcohol In 1,4-dioxane at 120℃; for 16h; Inert atmosphere; Sealed tube;
With methanol; sodium tetrahydridoborate at 0℃;
60 %Chromat. With ammsnium formate In isopropanol for 24h; Inert atmosphere; Irradiation; Sealed tube; Reaction conditions for the reduction of benzophenone derivatives: General procedure: The benzophenone (0.05 mmol), Ammonium formate (0.02g), 1D CdSTiO2 CSWs (0.02 g), and 5 ml i-PrOH were transferred into around bottom Pyrex flask (10 ml). Then the reaction mixture wasdegassed by argon gas, sealed with a septum, and irradiated by blue LED(3 W) for 24 h. After this time, the catalyst was simply separated bycentrifugation and the remaining solution was analyzed using thinlayeredchromatography (TLC) and the product yields were determinedby GC and HPLC. The desired product was extracted by platechromatography, and eluted with n-hexane/EtOAc. Assignments of theproducts were made by 1H NMR and 13CNMR spectroscopy.
60 %Chromat. With ammsnium formate In isopropanol for 24h; Inert atmosphere; Irradiation; Sealed tube; Reaction conditions for the reduction of benzophenone derivatives: General procedure: The benzophenone (0.05 mmol), Ammonium formate (0.02g), 1D CdSTiO2 CSWs (0.02 g), and 5 ml i-PrOH were transferred into around bottom Pyrex flask (10 ml). Then the reaction mixture wasdegassed by argon gas, sealed with a septum, and irradiated by blue LED(3 W) for 24 h. After this time, the catalyst was simply separated bycentrifugation and the remaining solution was analyzed using thinlayeredchromatography (TLC) and the product yields were determinedby GC and HPLC. The desired product was extracted by platechromatography, and eluted with n-hexane/EtOAc. Assignments of theproducts were made by 1H NMR and 13CNMR spectroscopy.
With sodium tetrahydridoborate; ethanol at 25℃;

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  • 2
  • [ 611-94-9 ]
  • [ 720-44-5 ]
  • [ 2443-45-0 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 66% With triethylamine In methanol for 6h; Irradiation;
1: 19% 2: 60% With aluminium; sodium chloride In ammonia at 25℃; for 4h; Irradiation;
1: 40% 2: 11% With TEA; cadmium(II) sulphide; thiophenol In N,N-dimethyl-formamide for 6h; Irradiation;
1: 26% 2: 33% With triethylamine In methanol for 6h; Irradiation;
1: 6% 2: 28% With triethylamine In acetonitrile for 6h; Irradiation;
1: 27% 2: 8% With triethylamine In acetonitrile for 6h; Irradiation;
With ethanol; aluminium amalgam
With SEC-BUTYLAMINE; 1-butyl-3-methylimidazolium Tetrafluoroborate Photolysis;

  • 3
  • [ 720-44-5 ]
  • [ 611-94-9 ]
YieldReaction ConditionsOperation in experiment
100% With oxygen; sodium acetate In water; dimethyl sulfoxide at 80℃; for 4h;
100% With oxygen; sodium hydroxide In water at 90℃; for 15h;
99% With potassium tetrakis-μ-pyrophosphitodiplatinate(II); tetrabutyl-ammonium chloride In dichloromethane; water at 20℃; for 8h; Inert atmosphere; Irradiation;
98% With oxygen; nitric acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 18h; Sealed tube;
98% With nickel(II) triflate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique;
97% With cobalt(III) acetate; sodium bromide In acetic acid at 60℃; for 1.5h;
97% With oxygen; caesium carbonate In α,α,α-trifluorotoluene at 105℃; for 20h; Air atmosphere; Ionic liquid; Aerobic Oxidation of Benzylic Alcohols General procedure: The oxidation of 1-phenyl-1-pentanol (1a) is representative (Table 2, entry 1): BMI-PF6 (85 mg, 0.30 mmol), 1-phenyl-1-pentanol (1a, 33 mg, 0.20 mmol), Cs2CO3 (33 mg, 0.10 mmol), and trifluoromethylbenzene (0.10 mL) were placed in a reaction flask with a reflux condenser and a drying tube lined with calcium chloride. The resulting mixture was stirred for 20 h at 105 °C. The reaction mixture was diluted with ethyl acetate and poured into water. The mixture was extracted with ethyl acetate three times. The combined organic layer was dried over Na2SO4, filtered through a pad of neutral alumina, and concentrated under reduced pressure. Purification by column chromatography on silica gel with hexane/ethyl acetate (10:1, v/v) as an eluent afforded 1-phenyl-1-pentanone (2a, 28 mg, 0.17 mmol) in 86% yield.
95% With bis<benzyltriethylammonium> dichromate In N,N,N,N,N,N-hexamethylphosphoric triamide at 60 - 80℃;
95% With nitric acid In nitromethane at 80℃; for 0.25h;
94% With 4-Benzoylpyridine In acetone at 20℃; for 23h; UV-irradiation; Inert atmosphere;
93% With 3,3-dimethyl-butan-2-one; dichlorotricarbonylruthenium(II) dimer; potassium phosphate tribasic trihydrate; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 100℃; for 24h; Inert atmosphere;
92% With iodine; oxygen In acetonitrile at 20℃; for 2.5h; Irradiation;
92% With sodium methylate; potassium iodide In methanol at 20℃; Electrochemical reaction;
92% With caesium carbonate; dimethyl sulfoxide at 125℃;
92% With tert.-butylhydroperoxide; sodium chloride; sodium hydroxide In water at 70℃; Sealed tube; Green chemistry;
91% With ammonium cerium (IV) nitrate; 1-hexyl-3-methylimidazolium hydrogen sulphate at 80℃; for 0.5h; neat (no solvent); chemoselective reaction;
91% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 80℃; for 0.5h; General Procedure General procedure: A mixture of alcohols (1 mmol) and DBDMH or DCDMH (1-1.5 mmol) in a 10 mL round-bottomed flask sealed with a stopper, was stirred in an oil-bath for the appropriate time and temperature (Table 1) under solvent-free condition. Then, as monitored by TLC (eluent n-hexane/acetone 10:2), hot water (10 mL) was added to mixture and stirred magnetically for 10 min. Then, the solution was extracted with (CH2Cl2/water (2 × 10 mL)) and organic phase dried over anhydrous Na2SO4 (1 g). Evaporation of the solvent gave the corresponding carbonyl compounds. Melting points and spectral data of all products are fully consistent with those previously reported. The structures of the products were confirmed from physical and spectroscopic data such as melting points, 1H NMR and 13C NMR spectra, fully consistent with those previously reported.17,18
91% With dirhodium tetraacetate; tributylphosphine; potassium carbonate In water at 90℃; for 24h; Inert atmosphere; Sealed tube;
91% With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;
90% With oxygen In acetonitrile at 20℃; for 1.25h; UV-irradiation;
90% With magnesium sulphate; vanadyl(IV) sulphate pentahydrate; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In water at 90℃; for 96h; 4.6 Oxidation of alcohols under open-air atmosphere General procedure: VOSO4·5H2O (126.5 mg, 0.5 mmol), 4,4′-di-tert-butyl-2,2′-bipyridyl (268.4 mg, 1 mmol), and p-nitrobenzhydrol (229.3 mg, 0.05 mmol) were placed in a 100 mL round-bottomed flask, and then water (50 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (18.06 g, 150 mmol) was slowly added into the mixture (cooling by ice water). After that, substrate (10 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 °C for the appropriate time under open-air atmosphere. After the reaction, the mixture was extracted with ethyl acetate and dried over anhydrous MgSO4. The extracts were concentrated in vacuo. Purification of the products was carried out by silica gel column chromatography using hexane and diethyl ether as eluent to afford the analytically pure ketones. In Table 7 (entries 3, 7, and 8), crude products were purified by recrystallization with ethyl acetate in refrigerator, afforded analytically pure ketones. The product was identified by comparison with the commercially available sample using 1H NMR spectroscopy.
89% With alumina supported chromium(VI) oxide In hexane for 24h; Ambient temperature;
88% With cesium hydroxide; air In toluene at 110℃; for 24h;
87% With palladium 10% on activated carbon; chlorobenzene; potassium hydroxide In methanol; water at 60℃; for 1h; Inert atmosphere; Procedure General procedure: The starting alcohol (1 mmol), KOH (3.0mmol) and catalyst (10 mol% Pd) were added to a Schlenkflask. In another Schlenk flask, the oxygen in the solvent(MeOH : H2O = 5:1, v/v, 6.0 mL) was removed by the freezepump-thaw and purging method. The aqueous solvent was transferred to the reaction flask of the starting alcohol by cannulation. Afterwards, chlorobenzene (3.0 mmol) was added using a syringe, and the reaction was kept under argon. Upon completion of the reaction based on TLC monitoring, the Pd/C was filtered off on celite and the solvent was removed by rotary evaporation. A brine solution was added to the residue and the product was extracted using methylene chloride. The organic layer was collected, dried with anhydrous magnesium sulfate, and concentrated byrotary evaporation. The mixture was purified via column chromatography using various hexane/EtOAc eluent systems. All products were known and characterized by comparing their 1H NMR spectra with those that have been published in the literature.
85% With Montmorillonite K10; ferric nitrate In hexane at 60℃; for 2h;
84% With oxovanadium(IV) sulfate; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In water at 90℃; for 6h;
84% With diisopropyl-carbodiimide In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;
83% With [VO(ReO4)(4,4'-di-tert-butyl-2,2'-bipyridine)2][0.25SO4*0.5ReO4]; oxygen In tetrahydrofuran; acetonitrile at 60℃; for 10h; Schlenk technique; chemoselective reaction; General procedure: General procedure: V1 (27.6 mg, 0.028 mmol) and substrate (0.5 mmol) were placed in a 20mL schlenk flask, and then the mixed MeCN/THF (1:1) solvent (3 mL) was added. The mixture was stirred at 60 C for an appropriate time under O2(balloon) or atmospheric air. After the reaction was completed, Et2O was added tothe reaction mixture. The resulting suspension was filtered and rinsed with Et2O. The combined filtrate was concentrated in vacuo. The yield of the oxidation products was confirmed by 1H NMR spectroscopy using 1,2-diphenylethane or 1,3,5-trimethoxybenzene as the internal standard. Purification of 2a-2c was performed by silica gel chromatography using hexane and EtOAc as the eluent to afford the analytically pure ketones. The isolated products were identified by comparing their 1H NMR spectra with those of authentic samples.
78% With 1,4-diaza-bicyclo[2.2.2]octane; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In toluene at 100℃; for 24h;
78% With air; MnO2 nanowires on amine functionalized graphite nanosheet In 1,4-dioxane at 100℃; for 12h;
73% With manganese(IV) oxide In dichloromethane at 20℃; for 11h; Inert atmosphere;
72% With <Mn3O(OAc)6(OAc)(HOAc)>*5H2O; lithium chloride In acetic acid for 0.2h; Heating;
51% With cerium(III) chloride heptahydrate; sodium hydrogencarbonate In acetonitrile at 50℃; for 42h; Irradiation; Sealed tube; General procedure (GP1) General procedure: A 10 mL glass vial equipped with a teflon-coated stirring bar was charged with benzylic alcohol 1 (0.2 mmol), CeCl3·7H2O (10 mol %), and NaHCO3 (10 mol%). The glass vial was sealed with a PTFE septum. Then, solvent (2 mL) was added and the reaction was opened to air via a needle. The reaction was placed in a pre-programed temperature (50 °C) controlled blue LED reactor (as shown in Figure S1) and the reaction mixture was irradiated with a 455 nm blue LED. After 35-48 hours, the reaction mixture was concentrated under reduced pressure. Product 2 was purified by flash chromatography on silica using hexane and AcOEt.
46% With N-Bromosuccinimide; potassium acetate In dichloromethane; water at 20℃; for 10h; Green chemistry; General Procedure for the Oxidative Reaction General procedure: A solution of diphenylmethanol (1 mmol), NBS (1.3equiv.), KOAc (1.5 equiv.) H2O (1.5 mL), and CH2Cl2 (0.5mL) was magnetically stirred in 25 mL flask at room temperaturefor 10 h. The reaction mixture was added into water(10 mL), and extracted with EtOAc (3 × 10 mL). The combinedEtOAc extracts were dried over anhydrous MgSO4,filtrated, and then the solvent was removed under reducedpressure. The residue was purified by the flash columnchromatography on silica gel with PE or PE/EtOAc as theeluent to obtain the desired products. The oxidation productswere identified by GC-MS and 1H NMR.
22% With potassium 12-tungstocobalt(III)ate; sodium tartrate buffer In water for 48h;
15% With tert.-butylhydroperoxide; chromium silicalite-2 In methanol for 1h; Heating;
With chromic acid
With bromine; sodium acetate In water; acetic acid at 35℃;
With bromine In acetic acid ΔE(activ.), ΔS(activ); further reagent - NBS, mercuric acetate;
With hydrogenchloride; chloramine-B In methanol; water at 34.9℃; ΔG(act.), ΔH(act.), ΔS(act); Ea; 303-318 K;
With hydrogenchloride; chloramine-B In methanol; water at 20 - 35℃;
With hydrogenchloride; ruthenium trichloride; chloroamine-T In methanol; water at 35℃; mechanistic study; Ea, ΔH, ΔS, ΔG; temperature dependence on rate constant (303-318 K);
With hydrogenchloride; N-bromo-p-toluenesulfonamide; sodium perchlorate; sodium In methanol; water at 35℃;
With potassium dichromate; sulfuric acid; Aliquat 336 In toluene at 64.84℃;
With N-bromophthalimide; mercury(II) diacetate; acetic acid In water at 29.84℃; for 24h;
With Jones reagent
94 %Chromat. With Iron(III) nitrate nonahydrate; sodium chloride In 1,2-dichloro-ethane at 20℃; for 8h;
With triethylamine; pyridinium chlorochromate In dichloromethane at 20℃;
Multi-step reaction with 2 steps 1: hypophosphorous acid; iodine / acetic acid / 60 °C 2: lithium perchlorate / acetonitrile; water / 5 h / 20 °C / Electrolysis
With sodium tetrahydroborate In methanol
With pyridinium chlorochromate In dichloromethane
With perchloric acid; tetrabutylammonium bromochromate In water; acetic acid at 29.84℃; Kinetic measurements: General procedure: A thermostatic water bath was used to maintain the desired temperature within ± 0.1 °C. The calculated amount of the reactants, i.e., benzhydrol (BH), TBABC, perchloric acid, acetic acid and water taken in a reaction vessel which was kept in a thermostatic water bath. After allowing sufficient time to attain the temperature of the experiment, arequisite amount of solutions were rapidly pipetted out into the spectrophotometric cell. The total volume of the reaction mixture was 5 mL in each case. Progress of the reaction was followed by measuring the decrease in [TBABC] by spectrophotometrically at 362 nm using UV-visible spectrophotometer, Shimadzu UV-1800 model. The reaction was carried under pseudo first-order conditions, i.e., [BH] >> [TBABC] in the presence of perchloric acid in 50 % acetic acid - 50 % water medium.
90 %Chromat. With dihydrogen peroxide In acetonitrile at 40℃; for 0.666667h; Green chemistry; chemoselective reaction; Catalytic oxidation of benzyl alcohols General procedure: In a typical procedure, benzyl alcohols (1 mmol), CH3CN(3 mL), H2O2(4 mmol), and MNPPILW (2 mg) were added to a 50 mL round bottom flask. The reaction mixture was stirred at 40 °C for a defined time. After the reaction,the catalyst was separated from the mixture by a magnet.The product was extracted by ethyl acetate (5 mL) and then analyzed by gas chromatography (GC).
82 %Chromat. With TiO2 supported on MIL-101 framework, modified with CdS nanocrystals and decorated with co-catalytic Ni nanoparticles (Ni/CdS/TiO2-MIL-101) In acetonitrile at 27℃; for 24h; Inert atmosphere; Irradiation;
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; Synthesis of S3 General procedure: To a solution of S2 (6 mmol) in DCM (20 mL), was added silica gel (about 10 g) and PCC (9.0 mmol, 1.5 equiv). Then the mixture was stirred for overnight at room temperature. The mixture was purified by chromatography eluted with DCM to give S3.
With ketoreductase-P1-B12; oxygen; NADPH; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 23℃; for 24h; Irradiation; Enzymatic reaction;
With polydopamine/MIL-53(Fe) nanocomposite; air In tetrachloromethane for 9h; Irradiation; chemoselective reaction;
91 %Chromat. With dihydrogen peroxide In water at 25℃; for 0.166667h; Sonication; Green chemistry; 2.3. Ultrasonic oxidation procedure General procedure: A mixture of benzyl alcohol (1 mmol), aqueous hydrogen perox- ide, and Co-ABDC/W as heterogeneous catalysis (0.01 g) was soni- cated in an ultrasonic bath (constant frequency) at 25 °C by circu- lating water. At the end of the oxidation, the mixture was diluted by adding ethyl acetate (3 ×15) to separate the product from the catalyst. The MOF was then washed and to be reused directly for a new procedure, without further purification.
With porous Fe-doped MIL-101/graphene nanohybrid In ethyl acetate for 8h; Inert atmosphere; 2.4 Evaluations of Photocatalytic Activity General procedure: A 500W xenon lamp with a 400nm cut off filter was usedto get the wave length () greater than 400nm visible lightto test the photocatalytic oxidation activity of catalysts atroom temperature. Firstly, 10mg catalyst and 0.1mmolalcohols were added into a quartz vial. Then the reactor wastreated under ultrasound for 1min and shaken to make surethat the catalyst was evenly dispersed in the solvent. Afterwards,the reacted solution was kept under dark for 2h inorder to insure that the construction of the alcohols’ adsorptionand desorption equilibriums on the catalyst surface. Inthe end, the samples were irradiated under visible light for8h. After the photocatalytic reaction, the conversion and the selectivity of the alcohols were obtained by the followformulas:where C0 is the concentration of alcohol before irradiation,Cn and Ca is the concentration of alcohol and aldehyde/ketone after irradiation via gas chromatograph (ShimadzuGC-2010) analysis.

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[50]Matic, Mirela; Denegri, Bernard; Kronja, Olga [European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1477 - 1486]
[51]Zheng, Lewei; Huang, Hongli; Yang, Chao; Xia, Wujiong [Organic Letters, 2015, vol. 17, # 4, p. 1034 - 1037]
[52]Hemalatha; Asghar, Basim H.; Mansoor, S Sheik [Asian Journal of Chemistry, 2018, vol. 30, # 4, p. 821 - 826]
[53]Maleki, Maryam; Baghbanian, Seyed Meysam; Tajbakhsh, Mahmood [Journal of the Iranian Chemical Society, 2018, vol. 15, # 2, p. 359 - 368]
[54]Tilgner, Dominic; Klarner, Mara; Hammon, Sebastian; Friedrich, Martin; Verch, Andreas; De Jonge, Niels; Kümmel, Stephan; Kempe, Rhett [Australian Journal of Chemistry, 2019, vol. 72, # 10, p. 842 - 847]
[55]Wang, Chunhai; Huang, Xiaoling; Liu, Xueting; Gao, Suqian; Zhao, Bin; Yang, Shangdong [Chinese Chemical Letters, 2020, vol. 31, # 3, p. 677 - 680]
[56]Betori, Rick C.; May, Catherine M.; Scheidt, Karl A. [Angewandte Chemie - International Edition, 2019, vol. 58, # 46, p. 16490 - 16494][Angew. Chem., 2019, vol. 131, p. 16642 - 16646,5]
[57]Meng, Shuangyan; Zeng, Wei; Wang, Mingming; Niu, Litong; Hu, Shaoping; Su, Bitao; Yang, Yaoxia; Yang, Zhiwang; Xue, Qunji [New Journal of Chemistry, 2020, vol. 44, # 5, p. 2102 - 2110]
[58]Aghajani, Zahra; Najafi, Gholam Reza; Sabaghi, Maryam [Journal of Organometallic Chemistry, 2020, vol. 925]
[59]Wang, Mingming; Ma, Yali; Lv, Bolin; Hua, Fenglin; Meng, Shuangyan; Lei, Xuedi; Wang, Qingtao; Su, Bitao; Lei, Ziqiang; Yang, Zhiwang [Catalysis Letters, 2021, vol. 151, # 8, p. 2384 - 2395]
  • 4
  • [ 720-44-5 ]
  • [ 6731-11-9 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; calcium chloride In dichloromethane
99% With hydrogenchloride In benzene for 0.5h;
99% With oxalyl dichloride In dichloromethane at 20℃; for 2h;
99% With hydrogenchloride; CaCl2 In benzene 1 p-methoxybenzhydryl chloride p-methoxybenzhydryl chloride A stirred suspension of p-methoxybenzhydryl alcohol (25.04 g, 0.117 mol) and CaCl2 (38.22 g, 0.344 mol) in benzene (400 mL) was bubbled with hydrogen chloride gas for 45 min. Afterwards, the mixture was stirred an additional 1 h and then filtered. The filtrate was evaporated to give the chloride (27.10 g, 99%) as an off-white solid. The structure was confirmed by 1 H--NMR in CDCl3.
79% With acetyl chloride In dichloromethane 1.) 0 deg C, 2.) room temperature, 1 h;
With hydrogenchloride; calcium chloride; Petroleum ether; benzene
With hydrogenchloride In benzene
With hydrogenchloride; calcium sulfate In dichloromethane
With thionyl chloride In chloroform for 0.166667h;
With hydrogenchloride; calcium chloride In dichloromethane at 0℃;
With thionyl chloride
With thionyl chloride Heating;
0.31 g With hydrogenchloride; calcium chloride In dichloromethane at -78 - 20℃;
With hydrogenchloride; calcium chloride In benzene
With hydrogenchloride; calcium chloride In dichloromethane; Petroleum ether; benzene
With pyridine; hydrogenchloride
With pyridine; acetyl chloride
With pyridine; thionyl chloride
Multi-step reaction with 2 steps 1: pyridine 2: concentrated aqueous HCl / oder Acetylchlorid
Multi-step reaction with 2 steps 1: pyridine 2: concentrated aqueous HCl / oder Acetylchlorid
Multi-step reaction with 2 steps 1: pyridine 2: concentrated aqueous HCl
With thionyl chloride In dichloromethane
With thionyl chloride In benzene Reflux;
With thionyl chloride In dichloromethane
With thionyl chloride In dichloromethane at 20℃; for 12h;

Reference: [1]Auricchio, Sergio; Magnani, Caterina; Truscello, Ada M. [European Journal of Organic Chemistry, 2002, # 14, p. 2411 - 2416]
[2]Brine, George A.; Boldt, Karl G.; Prakash, Doriswamy; Kotchmar, Dennis J.; Bondeson, Virginia C.; et al. [Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 1809 - 1814]
[3]Jönsson, Daniel [Tetrahedron Letters, 2002, vol. 43, # 27, p. 4793 - 4796] Jönsson, Daniel; Undén, Anders [Tetrahedron Letters, 2002, vol. 43, # 17, p. 3125 - 3128]
[4]Current Patent Assignee: ROCHE HOLDING AG - US6140137, 2000, A
[5]Strazzolini, Paolo; Giumanini, Angelo G.; Verardo, Giancarlo [Tetrahedron, 1994, vol. 50, # 1, p. 217 - 254]
[6]Norris; Blake [Journal of the American Chemical Society, 1928, vol. 50, p. 1811]
[7]Yung; Gilroy; Mahony [Journal of Pharmaceutical Sciences, 1978, vol. 67, # 7, p. 900 - 905]
[8]Nishida,S. [Journal of Organic Chemistry, 1967, vol. 32, p. 2692 - 2695]
[9]Takemura, Shoji; Azuma, Yoshiko; Shogaki, Chiyuki; Miki, Yasuyoshi; Nagatomi, Hikaru; et al. [Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 8, p. 2632 - 2638]
[10]Schneider, Reinhard; Mayr, Herbert; Plesch, Peter H. [Berichte der Bunsen-Gesellschaft, 1987, vol. 91, p. 1369 - 1374]
[11]Newman, Amy Hauck; Allen, Andrew C.; Izenwasser, Sari; Katz, Jonathan L. [Journal of Medicinal Chemistry, 1994, vol. 37, # 15, p. 2258 - 2261]
[12]Newman, Amy Hauck; Kline, Richard H.; Allen, Andrew C.; Izenwasser, Sari; George, Clifford; Katz, Jonathan L. [Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3933 - 3940]
[13]Van Pham, Thuy; McClelland, Robert A. [Canadian Journal of Chemistry, 2001, vol. 79, # 12, p. 1887 - 1897]
[14]Spange, Stefan; Adolph, Simone; Walther, Ralph; Zimmermann, Yvonne [Journal of Physical Chemistry B, 2003, vol. 107, # 1, p. 298 - 305]
[15]Denegri, Bernard; Streiter, Andre; Juric, Sandra; Ofial, Armin R.; Kronja, Olga; Mayr, Herbert [Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656]
[16]Balfe et al. [Journal of the Chemical Society, 1942, p. 605,610]
[17]Balfe et al. [Journal of the Chemical Society, 1942, p. 605,610]
[18]Balfe et al. [Journal of the Chemical Society, 1942, p. 605,610]
[19]Balfe et al. [Journal of the Chemical Society, 1942, p. 605,610]
[20]Balfe et al. [Journal of the Chemical Society, 1942, p. 605,610]
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[22]Streidl, Nicolas; Antipova, Anna; Mayr, Herbert [Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7328 - 7334]
[23]Location in patent: scheme or table Pajouhesh, Hassan; Feng, Zhong-Ping; Ding, Yanbing; Zhang, Lingyun; Pajouhesh, Hossein; Morrison, Jerrie-Lynn; Belardetti, Francesco; Tringham, Elizabeth; Simonson, Eric; Vanderah, Todd W.; Porreca, Frank; Zamponi, Gerald W.; Mitscher, Lester A.; Snutch, Terrance P. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1378 - 1383]
[24]Streidl, Nicolas; Mayr, Herbert [European Journal of Organic Chemistry, 2011, # 13, p. 2498 - 2506]
[25]Ana, Gloria; Kelly, Patrick M.; Malebari, Azizah M.; Noorani, Sara; Nathwani, Seema M.; Twamley, Brendan; Fayne, Darren; O’boyle, Niamh M.; Zisterer, Daniela M.; Pimentel, Elisangela Flavia; Endringer, Denise Coutinho; Meegan, Mary J. [Pharmaceuticals, 2021, vol. 14, # 2, p. 1 - 59]
  • 5
  • [ 720-44-5 ]
  • [ 834-14-0 ]
YieldReaction ConditionsOperation in experiment
94% With ethanol; nickel for 5h; Heating;
90% With 1,2-benzenedisulfonimide; isopropanol at 80℃; for 24h;
90% With gallium trifluoromethanesulfonate; isopropanol for 12h; Glovebox; Reflux;
90% With iodine; hypophosphorous acid; glacial acetic acid at 50℃; for 3.5h; Inert atmosphere; 2 Example 2: The preparation method of 4-methoxydiphenylmethane of the present embodiment comprises the following steps: (1), iodine (7.5g, 30mmol),4-Methoxydiphenylmethanol (6.5 g, 30 mmol)and acetic acid (190mL)Stir well under nitrogen protection in a flask equipped with a condenser,to obtain the first mixed solution,is the black solution;Among them, the temperature of stirring is 20 ,The stirring time was 3 min.Then add to the first mixtureHypophosphorous acid (50% aq., 15 mL; 145 mmol),The color of the solution gradually became lighter,to obtain the second mixture,That is, the final yellow-brown solution.(2), after dripping and heating the second mixed solution to 50°C,The heating time is 2.5h,Then stir for 1h,At this time, the solution was pale yellow and clear.TLC detection reaction was completed.Add 200mL of water to dilute,At this point the solution became cloudy,For the white suspension.Extract with PE (200mL),The aqueous phase was washed with 50 mL of PE,The combined organic phases were washed with saturated brine,After drying over anhydrous Na2SO4 in an oven at 45°C for 4 h, the solution was concentrated to obtain 5.5 g of pale yellow liquid.The purity is above 98%, and the yield is 90%.
87% With acridine; trifluoroacetic acid In dichloromethane Ambient temperature;
87% With acridane derivative; trifluoroacetic acid In dichloromethane for 2h; Ambient temperature;
84% Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With sodium tetrahydridoborate In acetonitrile at 0℃; for 0.25h; Inert atmosphere; Stage #2: With chloro-trimethyl-silane; potassium iodide In acetonitrile at 20℃; for 3h; Inert atmosphere; General Procedure for Reaction of 4a-c, 7, or 9a-b (General Procedure B) General procedure: Sodium borohydride (1.0 molar equiv.) was added to a solution of aryl alcohol (4a-c, 7, or 9a-b; 1.0 equiv.) in MeCN (2.0 mL) under an argon atmosphere at 0 °C. The mixture was stirred at 0 °C for 15 min. Trimethylsilyl chloride (2.0 equiv.) and potassium iodide (1.5 equiv.) were added to the mixture at 0 °C. The reaction mixture was stirred at rt under an argon atmosphere until no further TLC changes were observed. After the mixture was diluted with EtOAc (5 mL), the reaction was quenched by the addition of a saturated aqueous NaHCO3 solution (2 mL) and Na2S2O3 solution (2 mL). The layers were separated. The aqueous layer was extracted with EtOAc (5 mL). The combined organic layer was washed with water, brine, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel chromatography to give the corresponding product(s).
With lithium aluminium hydride; aluminium chloride anhydrous
With lithium aluminium hydride; aluminium chloride anhydrous In diethyl ether
With iodine; hypophosphorous acid In glacial acetic acid at 60℃;
With iodine; hypophosphorous acid In glacial acetic acid at 60℃;
Multi-step reaction with 2 steps 1: 4-dimethylaminopyridine; triethylamine / dichloromethane / 0 - 20 °C / Schlenk technique 2: N-ethyl-N,N-diisopropylamine; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N1,N1']bis[2-(2-pyridinyl-N)phenyl-C]iridium(III) hexafluorophosphate / water monomer; acetonitrile / 1 h / 40 °C / Sealed tube; Schlenk technique; Inert atmosphere; Irradiation
47 %Spectr. With 2,4,6-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-methylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)]PF6; triphenylphosphine In acetonitrile for 24h; Irradiation;

Reference: [1]Khim, Seock-Kyu; Dai, Mingshi; Zhang, Xuqing; Chen, Lei; Pettus, Liping; Thakkar, Kshitij; Schultz, Arthur G. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7728 - 7733]
[2]Location in patent: experimental part Barbero, Margherita; Bazzi, Stefano; Cadamuro, Silvano; Dughera, Stefano; Ghigo, Giovanni [European Journal of Organic Chemistry, 2009, # 25, p. 4346 - 4351]
[3]Sai, Masahiro [Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4330 - 4335]
[4]Current Patent Assignee: SHANGHAI TITAN TECH CO LTD - CN114292154, 2022, A Location in patent: Paragraph 0063-0070
[5]Singh, Serjinder; Gill, Sarbjeet; Sharma, Vijay K.; Nagrath, Sarita [Journal of the Chemical Society. Perkin transactions I, 1986, p. 1273 - 1276]
[6]Singh, Serjinder; Chhina, Sarbjeet; Sharma, Vijay K.; Sachdev, Satbir S. [Journal of the Chemical Society. Chemical communications, 1982, # 8, p. 453 - 454]
[7]Kato, Yuichi; Inoue, Tomoka; Furuyama, Yuuki; Ohgane, Kenji; Sadaie, Mahito; Kuramochi, Kouji [Tetrahedron Letters, 2021, vol. 86]
[8]Brown; White [Journal of the Chemical Society, 1957, p. 3755]
[9]Blackwell,J.; Hickinbottom,W.J. [Journal of the Chemical Society, 1961, p. 1405 - 1407]
[10]Zhang, Jintang; Wang, Zhentao; Wang, Ye; Wan, Changfeng; Zheng, Xiaoqi; Wang, Zhiyong [Green Chemistry, 2009, vol. 11, # 12, p. 1973 - 1978]
[11]Meng, Li; Su, Jihu; Zha, Zhenggen; Zhang, Li; Zhang, Zhenlei; Wang, Zhiyong [Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545]
[12]Rackl, Daniel; Kais, Viktor; Kreitmeier, Peter; Reiser, Oliver [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2157 - 2165]
[13]Stache, Erin E.; Ertel, Alyssa B.; Rovis, Tomislav; Doyle, Abigail G. [ACS Catalysis, 2018, vol. 8, # 12, p. 11134 - 11139]
  • 6
  • [ 720-44-5 ]
  • [ 57272-10-3 ]
YieldReaction ConditionsOperation in experiment
99% With trimethylsilylazide In dichloromethane at 25℃; for 1.5h; Inert atmosphere;
98% With trimethylsilylazide In dichloromethane at 20℃; for 16h;
98% With bismuth(lll) trifluoromethanesulfonate; trimethylsilylazide In dichloromethane at 20℃; for 0.0833333h; sec-Benzyl Azides 2: General Procedure General procedure: Bi(OTf)3 (1.0 mol%) was added to a solution of the appropriate secbenzylalcohol (1.0 equiv) and TMSN3 (1.2 equiv) in CH2Cl2 (4.0mL/mmol) at r.t. When the reaction was complete (TLC), the solventwas removed and the crude material was purified by column chromatography.
90% With trimethylsilylazide; zirconium(IV) chloride In acetonitrile at 0℃; for 0.5h; 1-(Azido(phenyl)methyl)-4-methoxybenzene (6) A stirred solution of alcohol 1 (2.0 g, 9.35 mmol) in acetonitrile (10 mL) at 0 °C was sequentially treated with azidotrimethylsilane (3.0 mL, 23.38 mmol) and ZrCl4 (0.22 g, 0.93mmol) and stirred for 30 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x10 mL). The combined organic layers were washed with brine (10 mL) and dried (Na2SO4). Solvent was evaporated and the residue purified by column chromatography (60-120 mesh Silica gel, 3% EtOAc in pet. ether) to afford 6 (2.02 g, 90%) as a yellow liquid; IR (CHCl3): 3030, 2091, 1609, 1510, 1243, 1174, 1031 cm-1; 1H NMR (300 MHz,CDCl3): δ 7.37-733 (m, 2H, ArH), 7.32 (m, 3H, ArH), 7.21 (d, 2H, J = 8.7 Hz, ArH), 6.88 (dt, 2H, J = 2.1, 8.8 Hz, ArH), 5.67 (s, 1H, ArCH), 3.97 (s, 3H, OMe); 13C NMR (75 MHz, CDCl3): δ 159.2, 139.7, 131.6, 128.6, 128.5,127.8, 127.1, 113.9, 67.9, 55.1.
87% With tetrafluoroboric acid diethyl ether; trimethylsilylazide In 1,2-dichloro-ethane at 60℃; for 0.25h;
With tris-(2-chloro-ethyl)-amine; benzene; trichloroacetic acid

  • 7
  • [ 720-44-5 ]
  • [ 108-24-7 ]
  • [ 38513-66-5 ]
YieldReaction ConditionsOperation in experiment
84% With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;
With pyridine
In pyridine for 14h; Heating;
  • 8
  • [ 123-11-5 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
92% In tetrahydrofuran; diethyl ether for 6h; Heating;
84% In tetrahydrofuran at 20℃; for 2h;
69% With 1-butyl-2-isopropyl-3-methylimidazolium triflimide In tetrahydrofuran at 20℃;
51% In diethyl ether at 0 - 20℃; for 8h;
With diethyl ether (+-)-4-methoxy-benzhydrol;
In diethyl ether at 0℃; for 2h;

  • 9
  • [ 720-44-5 ]
  • [ 107-99-3 ]
  • [ 524-99-2 ]
  • 10
  • [ 720-44-5 ]
  • [ 106-45-6 ]
  • [ 16928-62-4 ]
YieldReaction ConditionsOperation in experiment
96% With N-cetyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 0.25h; Schlenk technique;
With chloroform
  • 11
  • [ 534-22-5 ]
  • [ 720-44-5 ]
  • [ 90500-03-1 ]
YieldReaction ConditionsOperation in experiment
89% With copper(ll) bromide In 1,2-dichloro-ethane at 85℃; for 3h; 4.2. General procedure for alkylation of substituted furans andthiophenes with benzyl alcohols General procedure: Copper(II) bromide (33.5 mg, 0.15 mmol) was added to a stirred solution of alcohol 1 (1.5 mmol) and 2-substituted furan 2 (3.75 mmol for 2-methylfuran 2a; 1.5 mmol for 2-ethylfuran 2b, 2-tert-butylfuran 2c, 2-(4-chlorophenyl)furan 2d, 2,5-dimethylfuran 2e and 2-methylthiophene 2f) in DCE (4 mL) in a 5 mL Wheaton V-vial, containing a stirring bar and Teflon pressure cap. The microreactor was placed into a preheated (85 °C) aluminum block and the resulting solution stirred for 3 h at this temperature. After completion of the reaction, the mixture was concentrated in vacuo and the residue was purified by flash column chromatography (silica gel, petroleum ether/CH2Cl2) to afford the corresponding products.
79% With perchloric acid In acetic acid; benzene Heating;
  • 12
  • [ 104-92-7 ]
  • [ 100-52-7 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
99% With 1,10-Phenanthroline; 3-chloroprop-1-ene; trifluoroacetic acid; cobalt(II) bromide; zinc In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube;
96% With nickel(II) bromide 2-methoxyethyl ether complex; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In tetrahydrofuran at 60℃; for 16h; Sealed tube; Inert atmosphere;
91% With dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II); zinc In tetrahydrofuran at 75℃; for 24h;
88% Stage #1: 1-bromo-4-methoxy-benzene With magnesium; lithium chloride In tetrahydrofuran at 50℃; for 0.125h; Flow reactor; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 0.333333h; Flow reactor;
75% Stage #1: 1-bromo-4-methoxy-benzene With 4-methyltetrahydropyran; diisobutylaluminium hydride; magnesium In hexane at 60℃; for 3h; Inert atmosphere; Green chemistry; Stage #2: benzaldehyde In hexane at 0 - 20℃; for 1h; Inert atmosphere; Green chemistry;
70% Stage #1: 1-bromo-4-methoxy-benzene With TurboGrignard In tetrahydrofuran at 20℃; for 72h; Stage #2: benzaldehyde In tetrahydrofuran at 0℃; for 0.333333h;
51% In N,N-dimethyl-formamide Electrochemical reaction; stainless steel (Fe/Cr/Ni = 72/18/10) anode;
With magnesium
57 % Chromat. With lithium Sn In tetrahydrofuran at 20℃; for 0.166667h;
Stage #1: 1-bromo-4-methoxy-benzene; benzaldehyde With magnesium In tetrahydrofuran at 20 - 85℃; for 2h; Stage #2: In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #1: 1-bromo-4-methoxy-benzene With iodine; magnesium In diethyl ether for 0.5h; Reflux; Stage #2: benzaldehyde In diethyl ether for 0.5h; Reflux;
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;

Reference: [1]Presset, Marc; Paul, Jérôme; Cherif, Ghania Nait; Ratnam, Nisanthan; Laloi, Nicolas; Léonel, Eric; Gosmini, Corinne; Le Gall, Erwan [Chemistry - A European Journal, 2019, vol. 25, # 17, p. 4491 - 4495]
[2]Garcia, Kevin J.; Gilbert, Michael M.; Weix, Daniel J. [Journal of the American Chemical Society, 2019, vol. 141, # 5, p. 1823 - 1827]
[3]Majumdar, Kanak Kanti; Cheng, Chien-Hong [Organic Letters, 2000, vol. 2, # 15, p. 2295 - 2297]
[4]Huck, Lena; De La Hoz, Antonio; Díaz-Ortiz, Angel; Alcázar, Jesus [Organic Letters, 2017, vol. 19, # 14, p. 3747 - 3750]
[5]Kobayashi, Shoji; Tamura, Tomoki; Yoshimoto, Saki; Kawakami, Takashi; Masuyama, Araki [Chemistry - An Asian Journal, 2019, vol. 14, # 21, p. 3921 - 3937]
[6]Krasovskiy, Arkady; Knochel, Paul [Angewandte Chemie - International Edition, 2004, vol. 43, # 25, p. 3333 - 3336]
[7]Durandetti, Muriel; Perichon, Jacques; Nedelec, Jean-Yves [Tetrahedron Letters, 1999, vol. 40, # 51, p. 9009 - 9013]
[8]Touiti, Dominique; Jost, Roland; Sommer, Jean [Journal of the Chemical Society. Perkin transactions II, 1986, p. 1793 - 1798]
[9]Rieke, Reuben D.; Lee, Jun-Sik; Kye, Young-Sik; Harbison, Gerard S. [Journal of Organometallic Chemistry, 2004, vol. 689, # 21, p. 3421 - 3425]
[10]Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie [Organic Letters, 2012, vol. 14, # 18, p. 4850 - 4853,4]
[11]Pan, Xiaojuan; Li, Minghao; Gu, Yanlong [Chemistry - An Asian Journal, 2014, vol. 9, # 1, p. 268 - 274]
[12]Shigeno, Masanori; Hayashi, Kazutoshi; Nozawa-Kumada, Kanako; Kondo, Yoshinori [Chemistry - A European Journal, 2019, vol. 25, # 24, p. 6077 - 6081]
  • 13
  • [ 720-44-5 ]
  • [ 123-54-6 ]
  • [ 53786-86-0 ]
YieldReaction ConditionsOperation in experiment
98% With iron(III) chloride In dichloromethane for 4h; Heating;
89% In 1,1,2,2-tetrachloroethane for 9.5h; Reflux;
88% In dichloromethane at 60℃; for 4h; Sealed tube; 4.2.12 3-((4-Methoxyphenyl) (phenyl)methyl)pentane-2,4-dione (15) General procedure: 4.1.2 Typical procedure for direct benzylation of 1,3-dicarbonyl derivatives using alcohols as alkylating agents catalyzed by 1a: To a 10mL sealed tube was added dibenzoylmethane (112 mg, 0.5 mmol), benzhydrol (101 mg, 0.55 mmol), CH2Cl2 (2 mL) and catalyst (39.8 mg, 5 mol%). The mixture was stirred at 60 °C for 4 h. Then the reaction mixture was evaporated in vacuum, CH2Cl2 (3×10 ml) was added to the reaction mixture and the catalyst was filtered for the next cycle of reaction. The combined CH2Cl2 solution was removed by evaporation in vacuum and was then subject to silica gel column chromatograph; the product (4) was obtained: 185 mg, isolated yield 95 %
85% With tin ion-exchanged montmorillonite In 1,2-dichloro-ethane at 100℃;
62% With silica gel supported sodium hydrogen sulfate In 1,1-dichloroethane at 80℃; for 0.5h;
With sulfuric acid

  • 15
  • [ 940-00-1 ]
  • [ 100-52-7 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
91% In tetrahydrofuran at 60℃; for 2h;
91% With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In tetrahydrofuran at 60℃; for 2h;
  • 16
  • [ 934-56-5 ]
  • [ 123-11-5 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
85% In tetrahydrofuran at 60℃; for 24h;
85% With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In tetrahydrofuran at 60℃; for 24h;
74% With rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate In water at 110℃; for 12h;
  • 17
  • [ 720-44-5 ]
  • [ 1886-57-3 ]
  • 2-tert-butyl-4-[(4-methoxyphenyl)methyl]nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,2,3-Benzotriazole; potassium <i>tert</i>-butylate 1) perfluorocarbon fluid (bp 104 deg C), reflux, overnight; 2) THF, -20 deg C, 4 h; Yield given. Multistep reaction;
  • 18
  • diphenyliodonium tetrafluoroborate [ No CAS ]
  • [ 123-11-5 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
72% With chromium dichloride; nickel dichloride In N,N-dimethyl-formamide for 5h; Ambient temperature;
72% With chromium dichloride; nickel dichloride In N,N-dimethyl-formamide at 25℃; for 5h;
  • 19
  • [ 720-44-5 ]
  • [ 622-46-8 ]
  • Phenyl N-(4-methoxybenzhydryl)carbamate [ No CAS ]
  • 20
  • [ 123-11-5 ]
  • [ 98-80-6 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
99% With tri-tert-butyl phosphine In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 25 - 28℃; for 16h;
99% With potassium-t-butoxide; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 90℃; for 1h;
99% With Rh<SUB>2</SUB>(trifluoroacetate)<SUB>4</SUB>(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)<SUB>2</SUB>; potassium-t-butoxide In methanol at 60℃; for 4h; Inert atmosphere;
99% With ϖ-allylpalladium (II) chloride dimer; 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-4,5-dihydroimidazolinium chloride; Cs2CO3 In 1,4-dioxane at 80℃; for 3h; Inert atmosphere; Sealed tube; General procedure for the palladium catalyzed arylation of aldehyde 2a-m using arylboronic acid 3a-h General procedure: Palladium source (0.01 mmol), imidazolinium salt 1 (0.01 mmol), phenylboronic acid (1.50 mmol) and an inorganic base (2.0 mmol) were charged ina 10 mL test tube sealed with a rubber septum. The test tube was evacuated and backfilled with argon. This sequence was repeated five times. Then solvent (2 mL) and aldehyde (1.0 mmol) were added via the rubber septum with syringe. In an argon flow, therubber septum was replaced with a Teflon liner screw cap. The test tube was placed in an oil bath preheated at 80 C. The reaction mixture was stirred for 2-12 h and then cooled to room temperature. Next, operation of (i) or (ii) was performed. (i) The obtained crude was purified by passing it through a silica gel column witha hexane/ethyl acetate eluent (Table 2 entry 1, Tables 3 and 5 entries1e7). (ii) Diphenylmethane (168 mg, 1.0 mmol) as an internal standard was added and then an aliquot of the organic layer of thereaction mixture was subjected to the quantitative analysis by 1H NMR (Tables 1 and 2).
99% With chlorobis(cyclooctene)rhodium(I) dimer; (diphenylphosphino)(phenyl)methanone; anhydrous sodium carbonate In lithium hydroxide monohydrate; toluene at 60℃; Schlenk technique; Inert atmosphere; General procedure B for Table 2 General procedure: To a Schlenk tube was charged with [RhCl(coe)2]2(1.1 mg, 1 mol % to Rh) , ligand L1(1.0 mg, 1.1 eq to Rh) and 1 mL toluene, the mixture was stirred at room temperature for 30 min. Then ArB(OH)2 (0.75 mmol), aldehyde (0.3mmol) and aqueous Na2CO3 (0.5 mL, 1.5 M, 0.75 mmol) was added. The mixture was stirred to react at 60°C. After the reaction completed (monitored by TLC), water (5 mL) was added to the mixture. The organic materials were extracted with ethyl acetate for three times and the combined organic layer were washed with brine and dried over Na2SO4.The solvent was evaporated, and the residue was purified by silica-gel column chromatography (petroleum ether/ethyl acetate, 10/1 ) to give the desired product.
97% With potassium-t-butoxide In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 90℃; for 1h;
93% With sodium methoxide; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 80℃; for 0.5h;
90% With tripotassium phosphate tribasic In toluene at 20℃; for 48h;
90% Stage #1: phenylboronic acid With trimethyl gallium In toluene at 20℃; for 2h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In toluene at 20℃; for 3h; Inert atmosphere;
89% With 1,3-bis(2,4,6-trimethylbenzyl)perhydrobenzimidazolinium chloride; bis[chlorido(η2,η2-cycloocta-1,5-diene)rhodium(I)]; potassium-t-butoxide In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 60℃; for 5h;
87% With tripotassium phosphate tribasic; platinacycle In toluene at 60 - 80℃;
81% With -(2,4,6-trimethylphenyl)imidazolio]methyl}benzene hexabromide; potassium-t-butoxide In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 24h;
81% With 1-(2,6-diisopropylphenyl)-3-(2-(phenylthio)phenyl)-4,5-dihydroimidazolinium chloride; ϖ-allylpalladium (II) chloride dimer; Cs2CO3 In lithium hydroxide monohydrate at 20 - 100℃;
81% With C62H74Cl2N4Pd2S2; Cs2CO3 In 1,4-dioxane at 70℃; for 3h; Inert atmosphere; Sealed tube;
78% With [(quinone)Rh(COD)]-*K+; lithium hydroxide monohydrate at 75℃; for 3h;
78% In lithium hydroxide monohydrate at 75℃; for 3h; 24 Distilled water (2 mL) was added to an elongated 15 mL-Schlenk flask. The water was bubbled for 5 minutes with nitrogen gas. After bubbling, the catalyst K+3- (15 mg, 0.024 mmol), phenylboronic acid (0.15 g, 1.23 mmol) and benzaldehyde (0.1 ml, 0.98 mmol) were added. The mixture solution was heated at 75° C. for 3 hours. After reaction, the solution was cooled to room temperature and CDCl3 (3.5 mL) was added. The solution was shaken for 1 minute and the CDCl3 part was directly analyzed by 1H NMR. The yield was calculated by the comparison of peak area of aldehyde reactant and the benzyl proton of the product alcohol.
77% With tris (α-naphthyl)phosphine; palladium diacetate; potassium carbonate In lithium hydroxide monohydrate at 20 - 65℃; for 15h; Ionic liquid; Inert atmosphere; Schlenk technique; Green chemistry; General procedure for the palladium-catalyzed addition of arylboronic acids to aldehydes in [bmim][PF6]/H2O General procedure: A Schlenk reaction tube was charged with [bmim][PF6] (3mL), distilled water (2mL), Pd(OAc)2 (0.05mmol), P(1-Nap)3 (0.05mmol), aldehyde (1.0mmol), aryl-boronic acid (2.0mmol), and K2CO3 (3.0mmol) under an argon atmosphere. The mixture was stirred at room temperature for 0.5h, and then heated at 65°C for 6-24h. After being cooled to room temperature, the reaction mixture was extracted three times with diethyl ether (3×10mL). The residue of the extraction was subjected to a second run of the addition reaction by charging with the same substrates (arylboronic acid, aldehyde, and K2CO3) under the same conditions without further addition of Pd(OAc)2 or P(1-Nap)3. The combined ether phase was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (hexane-ethyl acetate=10:1) to give the desired product.
74% With bis(acetylacetonato)nickel(II); potassium carbonate In toluene at 180℃; for 0.166667h; Microwave irradiation; General procedure for the Ni-catalyzed arylation of aldehydes with arylboronic acids (Table 2): Aldehyde (1.0 mmol), arylboronic acid (1.5 mmol, 1.5 equiv), K2CO3 (138 mg, 1.0 mmol, 1 equiv), and Ni(acac)2 (2.6 mg, 0.01 mmol, 1 mol %) were added to a 10 mL microwave processing vial containing a Teflon coated stir bar. After the vial was sealed dry toluene (2 mL) was transferred to the vial and mixture was pre-stirred for 5 min. The vial was placed in the microwave cavity and heated for 10 min at 180 °C (fixed hold time). After cooling, diethyl ether or ethyl acetate (10 mL) was added and the crude reaction mixture was subsequently washed with 25% aqueous NH3 (2 × 10 mL). The aqueous ammonium layer was reextracted again with diethyl ether or ethyl acetate (2 × 10 mL). The combined organic phase was dried over MgSO4 and the residue after evaporation purified by flash chromatography using a petroleum ether/ethylacetate (10:1-2.5:1) as eluent phase.
72% With tripotassium phosphate monohydrate; Ni(ClO4)2·6H2O In isopropanol at 80℃; Inert atmosphere;
67% With potassium carbonate In tetrahydrofuran at 65℃; for 24h;
59% With sodium hydroxide; Rhodium trichloride; t-Bu-Amphos In acetonitrile at 80℃; for 2h;
57% Stage #1: phenylboronic acid With cobalt(II) 2,4-pentanedionate; 1,2-(diphenylphosphino)ethane In tetrahydrofuran; acetonitrile Sealed tube; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere;
56% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; Cs2CO3; triphenylphosphine In chloroform; toluene at 80℃; for 24h;
56% With tris(dibenzylideneacetone)dipalladium(0)-chloroform; Cs2CO3; triphenylphosphine In toluene at 80℃; for 24h; Inert atmosphere;
53% With potassium-t-butoxide In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 6h;
17% With silver(I) nitrate In nitromethane at 80℃; for 48h; 2.3 Catalyst Testing General procedure: PdCl2SZU-1 (10 mg, 1.0 mol%) and AgNO3(5mg,2.0mol%) were mixed in CH3NO2(2mL), and stirred at80°C for 1h, then 1mmol arylboronic acid and 0.5mmolaromatic aldehyde added. The reaction was carried out for24h. During the reaction, an appropriate amount of arylboronicacid could be added. The reaction mixture was concentratedand the target product was purified by column chromatographyon silica gel to determine the catalyst efficiency.
14% In nitromethane at 50℃; for 5h;
96 % Chromat. With potassium-t-butoxide In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 80℃; for 1h;
With tri-tert-butyl phosphine; potassium carbonate In 1,4-dioxane; propan-2-one at 80℃; for 24h;
38 %Spectr. With [Rh(2,5-norbornadiene)(chloride)(1-(2-NHBoc-ethyl)-3-methyl-imidazolin-2-ylidene)]; potassium-t-butoxide; lithium hydroxide monohydrate In 1,2-dimethoxyethane at 80℃; for 8h; Inert atmosphere;
91 %Chromat. With C32H44ClN2Rh; potassium-t-butoxide In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;
Stage #1: 4-methoxy-benzaldehyde With tripotassium phosphate tribasic; C9H4O6(2-)*Ni(2+)*C10H8N2 In butan-1-ol Green chemistry; Stage #2: phenylboronic acid In butan-1-ol at 100℃; for 6h; Green chemistry;
90 %Spectr. With C28H41N2ORh; potassium-t-butoxide In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 80℃; for 0.25h; Inert atmosphere; General procedure for the arylation of aldehydes General procedure: Phenylboronic acid (2 mmol), rhodium complex (0.01mmol) and KOtBu (1 mmol) were successively added to a two-necked flask and the vessel was evacuated andf lushed with argon three times. DME (3 mL) and H2O (1mL) were syringed, and then the aldehyde (1 mmol) was added to the mixture. The mixture was heated to 80 °C for 15 min. After cooling to ambient temperature,the reaction mixture was diluted with ethyl acetate (15 mL) and washed with water (5 mL). The organic phase was dried (Na2SO4) and evaporated in vacuo. The residue was purified by preperativeTLC (petrol ether/ethyl acetate 12:1). Yields were determined by 1H NMR. Enantiomeric excesses were determined by HPLC using chiral column.
66 %Spectr. With bis[chlorido(η2,η2-cycloocta-1,5-diene)rhodium(I)]; C22H28Cl3N2O5(1+)*Br(1-); potassium-t-butoxide In methanol; 1,2-dimethoxyethane at 80℃; for 4h; Inert atmosphere; 3.5. General procedure for the arylation of aldehydes General procedure: Phenylboronic acid (1 mmol), ligand (or complex 3a) (0.01 mmol), [RhCl(COD)]2 (0.005 mmol), and KOtBu (0.5 mmol) were successively added to a two-necked ask. The vessel was evacuated and flushed with argon three times. MeOH (1.5 mL) and DME (0.5 mL) were syringed, and then the aldehyde (1 mmol) was added to the mixture. The mixture was heated to 80°C for 1 or 4 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (3 mL) and washed with water (2 mL). The organic phase was dried(Na2SO4) and evaporated in a vacuum. Yields were determined by 1H NMR. The enantiomeric excesses were determined by HPLC using a chiral OJ-H column.
With rhodium(II) acetate dimer; sodium hydroxide; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In 1,4-dioxane; lithium hydroxide monohydrate at 40℃; for 6h; Inert atmosphere;
With chlorotris(triphenylphosphine) rhodium (I); anhydrous sodium carbonate In lithium hydroxide monohydrate at 110℃; for 12h; Inert atmosphere; Sealed tube; General procedure for the synthesis of 3. General procedure: A sealed tube equipped witha magnetic stirrer bar was charged with 1 (0.2 mmol), 2 (0.3 mmol,1.5 equiv.), Rh(PPh3)3Cl (0.5 mol% or 1 mol%), Na2CO3 (0.3 mmol,1.5 equiv.) and GVL/H2O (1 : 1, 2 ml) under N2. The reaction mixture was then heated to 110 °C and stirred for 6-12 h (for details, see Online Supplementary Materials). Upon reaction completion, the resulting solution was quenched with water and extracted with ethyl acetate. The collected organic extracts were dried over Na2SO4. The solvent was then removed under reduced pressure and the residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (10 : 1) as eluent to afford the product (3aa-ar or 3ba-qa).

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[2]Trindade, Alexandre F.; Gois, Pedro M. P.; Veiros, Luis F.; Andre, Vania; Duarte, M. Teresa; Afonso, Carlos A. M.; Caddick, Stephen; Cloke, F. Geoffrey N. [Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4076 - 4086]
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[7]Fuerstner, Alois; Krause, Helga [Advanced Synthesis and Catalysis, 2001, vol. 343, # 4, p. 343 - 350]
[8]He, Ping; Lu, Yong; Hu, Qiao-Sheng [Tetrahedron Letters, 2007, vol. 48, # 30, p. 5283 - 5288]
[9]Location in patent: body text Jia, Xuefeng; Fang, Ling; Lin, Aijun; Pan, Yi; Zhu, Chengjian [Synlett, 2009, # 3, p. 495 - 499]
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[16]Current Patent Assignee: BROWN UNIVERSITY - US2007/117981, 2007, A1 Location in patent: Page/Page column 5; 7
[17]Zhao, Hong; Cheng, Mingzhu; Zhang, Tinli; Cai, Mingzhong [Journal of Organometallic Chemistry, 2015, vol. 777, p. 50 - 56]
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  • 21
  • [ 780-69-8 ]
  • [ 123-11-5 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydroxide; cyclo-octa-1,5-diene In 1,4-dioxane at 90℃; for 16h;
  • 22
  • [ 4028-23-3 ]
  • [ 720-44-5 ]
  • [ 124494-12-8 ]
YieldReaction ConditionsOperation in experiment
82% With indium(III) chloride In dichloromethane at 20℃; for 0.166667h;
  • 23
  • [ 623-12-1 ]
  • [ 100-52-7 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 4-chloromethoxybenzene With iodine; magnesium In tetrahydrofuran at 150℃; for 1h; microwave irradiation; Stage #2: benzaldehyde In tetrahydrofuran at 100℃; for 0.5h; microwave irradiation;
  • 24
  • [ 5720-07-0 ]
  • [ 100-52-7 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
95% With potassium <i>tert</i>-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tert-Amyl alcohol at 60℃; for 2h;
91% With [(quinone)Rh(COD)]-*K+; water at 75℃; for 3h;
91% In water at 75℃; for 3h; 30 Distilled water (2 mL) was added to an elongated 15 mL-Schlenk flask. The water was bubbled for 5 minutes with nitrogen gas. After bubbling, the catalyst K+3- (15 mg, 0.024 mmol), phenylboronic acid (0.15 g, 1.23 mmol) and benzaldehyde (0.1 ml, 0.98 mmol) were added. The mixture solution was heated at 75° C. for 3 hours. After reaction, the solution was cooled to room temperature and CDCl3 (3.5 mL) was added. The solution was shaken for 1 minute and the CDCl3 part was directly analyzed by 1H NMR. The yield was calculated by the comparison of peak area of aldehyde reactant and the benzyl proton of the product alcohol.
88% With bis(1,5-cyclooctadiene)diiridium(I) dichloride; tris(2,4-di-tert-butylphenyl)phosphite; potassium carbonate In 1,4-dioxane at 60℃; Glovebox; Inert atmosphere; General procedure for Iridium (I)-catalyzed addition reactions of arylboronic acids with aldehydes: General procedure: In a glove-box with N2 atmosphere, [Ir(COD)Cl]2 (0.00125 mmol), tris(2,4-di-t-butylphenyl)phosphite 1 (0.0025 mmol) and 1,4-dioxane (0.2 mL) were placed in a vial. Then the vial containing the mixture was sealed and taken out of glove-box and heated in 110 oC of oil bath with stirring for 30 minutes. When the preparation of catalyst was completed, the vial was cooled to room temperature and brought into the glove-box again and followed by the addition of 1,4-dioxine (0.8 mL), aldehyde (0.25 mmol), arylboronic acids (0.375 mmol), and K2CO3 (0.75 mmol). After the mixture was stirred at 60 oC for 6-10 hours, the reaction was quenched by adding a small amount of water. Extraction with ethyl acetate followed by column chromatography on silica gel with ethyl acetate/hexane (v/v=1:10) afforded the alcohols.
84% With potassium <i>tert</i>-butylate In 1,4-dioxane; water at 80℃; for 6h;
79% With sodium hydroxide; rhodium(III) chloride; t-Bu-Amphos In acetonitrile at 80℃; for 2h;
72% With potassium phosphate monohydrate; nickel(II) perchlorate hexahydrate In isopropyl alcohol; toluene at 80℃; Inert atmosphere;
50% With sodium hydroxide In 1,2-dimethoxyethane; water at 80℃; for 8h;
31% With chlorobis(cyclooctene)rhodium(I) dimer; α-Oxo-phenylmethan-diphenylphosphin; sodium carbonate In water; toluene at 60℃; Schlenk technique; Inert atmosphere; General procedure B for Table 2 General procedure: To a Schlenk tube was charged with [RhCl(coe)2]2(1.1 mg, 1 mol % to Rh) , ligand L1(1.0 mg, 1.1 eq to Rh) and 1 mL toluene, the mixture was stirred at room temperature for 30 min. Then ArB(OH)2 (0.75 mmol), aldehyde (0.3mmol) and aqueous Na2CO3 (0.5 mL, 1.5 M, 0.75 mmol) was added. The mixture was stirred to react at 60°C. After the reaction completed (monitored by TLC), water (5 mL) was added to the mixture. The organic materials were extracted with ethyl acetate for three times and the combined organic layer were washed with brine and dried over Na2SO4.The solvent was evaporated, and the residue was purified by silica-gel column chromatography (petroleum ether/ethyl acetate, 10/1 ) to give the desired product.

  • 25
  • [ 100-52-7 ]
  • [ 155826-85-0 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
88% With 4-Octyne; water In 1,4-dioxane at 80℃; for 12h;
  • 26
  • [ 123-11-5 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
97% With tri-tert-butyl phosphine In water; toluene at 60℃;
  • 27
  • [ 720-44-5 ]
  • [ 100-01-6 ]
  • N-(4-nitrophenyl)-1-phenyl-1-(4-methoxyphenyl)methylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane at 20℃; for 16h;
82% With sodium tetrachloroaurate(III) dihydrate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 80℃; for 16h; Sealed tube; Green chemistry; General Procedure General procedure: A mixture of aniline 1 (1 mmol), NaAuCl4·2H2O (20 mg, 0.05 mmol), sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) (18 mg, 0.05 mmol) and benzylic alcohol 2 (1.2 mmol) in H2O (4 mL) was heated at 80 °C for 16 h in a sealed tube under air. After cooling, the reaction mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes/EtOAc) to give desired product 3.
75% With iron(III) chloride at 60℃; neat (no solvent);
  • 28
  • [ 720-44-5 ]
  • [ 141-97-9 ]
  • ethyl 2-(4-methoxyphenylphenylmethyl)acetoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With iron(III) chloride In dichloromethane for 5h; Heating;
Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol; ethyl acetoacetate In dichloromethane at 0℃; for 0.166667h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 0 - 20℃; for 24h; regioselective reaction; General procedure for the one-pot coulping/cyclization reaction to synthesis the indene derivatives 3a-3u. General procedure: A 50 mL round-bottom flask was charged with benzyllic alcohols (1 mmol), 1,3-dicarbonyl compounds (1.2 mmol), anhydrous CH2Cl2 (20 mL) and a stirring bar. After the solution was cooled to 0°Ca and stirred for 10 mintues, CF3SO3H (2 mmol) was added portionwise and then the reactions mixture was allowed to reach rt. The mixture was stirred for 2 hours at rt till benzylic alcohols disappeared completely, 2 mL water poured into the flask, and the mixture extracted with ethyl acetate (3×15 mL). The combined organic layers were dried with anhydrous Na2SO4, and concentrated in vacuo. The residue was isolated by flash column chromatography on silica gel or thin-layer chromatograms b to give the products.
  • 29
  • [ 3262-89-3 ]
  • [ 123-11-5 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: triphenylboroxine With bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; 4-chlorobenzophenone In tetrahydrofuran at 20℃; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 20℃;
86% With sodium t-butanolate In 1,2-dimethoxyethane; water at 100℃; for 48h;
86% With bis(1,5-cyclooctadiene)nickel(0); (+/-)-Et-Duphos; sodium t-butanolate In 1,2-dimethoxyethane; water at 100℃; for 48h;
  • 30
  • [ 2996-92-1 ]
  • [ 123-11-5 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
73% With tetrabutyl ammonium fluoride In acetonitrile at 120℃; for 0.5h; microwave irradiation;
  • 31
  • [ 720-44-5 ]
  • [ 762-72-1 ]
  • [ 124494-12-8 ]
YieldReaction ConditionsOperation in experiment
98% With Sn-montmorillonite In dichloromethane at 20℃;
98% With 3-dodecyl-2-iodo-1-methyl-1H-imidazol-3-ium hexafluoroantimonate; iodine In nitromethane at 20℃; for 2h; Inert atmosphere;
97% With H+-exchanged montmorillonite In n-heptane at 60℃; for 1h;
97% With tetrafluoroboric acid diethyl ether In 1,2-dichloro-ethane at 60℃; for 0.25h; Allylation of the Benzhydryl alcohols General procedure: In a 2 mL vial containing the a stir bar, the indicated benzhydrol alcohol (1.0 equiv) and allyltrimethylsilane (1.3 equiv) were added followed by addition of anhydrous 1,2-dichloroethane (0.7 mL). The mixture was allowed to stir for a minute at 60°C. HBF4.OEt2 (0.4-1.4 equiv) was added dropwise and the reaction was further allowed to stir for 15 min. The reaction was quenched with 20 mL of water and extracted in 20 mL of ethyl acetate. The organic layer was washed with water (3×15 mL) followed by brine (1×10 mL). The organic layer was dried with MgSO4 and concentrated. The purification procedures varied based on the product synthesized. The specific details are given below. In the cases where a CH3CN/hexane extraction was required, the product was solubilized in 5 mL of anhydrous CH3CN in a 20 mL vial. Then, 1 mL of hexane was added, forming a bilayer. The two layers were allowed to mix thoroughly and then settle in an ice bath. The bottom acetonitrile layer was then removed and concentrated.
94% With scandium tris(trifluoromethanesulfonate) In acetonitrile at 40℃; for 1h; Inert atmosphere;
93% With o-benzenedisulfonimide at 20 - 25℃; for 0.25h; neat (no solvent);
79% With 1,1,1,3',3',3'-hexafluoro-propanol; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate In dichloromethane at 20℃; for 16h; Inert atmosphere; Sealed tube; 1-Methoxy-4-(1-phenylbut-3-en-1-yl)benzene (22). To a 2 mL vial, flushed with argon, was added (4-methoxyphenyl)(phenyl)methanol (72.1 mg, 0.34 mmol, 1 equiv.) and dry dichloromethane (1.21 mL). To this solution was added successively allyltrimethylsilane (274 μL, 1.68 mmol, 5 equiv.), hexafluoroisopropanol (0.14 mL) and XtalFluor-E (85 mg, 0.37 mmol, 1.1 equiv.). The vial was sealed and the reaction was stirred at room temperature for 16 h. The reaction was quenched with water and extracted with dichloromethane (3 x 2 mL), dried with MgSO4 and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexanes/EtOAc(98/2) as the eluent. The desired product (63.2 mg, 79%) was obtained as white solid. Spectroscopic data was in agreement with the literature.

  • 32
  • [ 720-44-5 ]
  • [ 79-22-1 ]
  • [ 940934-41-8 ]
YieldReaction ConditionsOperation in experiment
86% With pyridine; dmap In dichloromethane at 0 - 20℃; for 2.5h;
80% With pyridine In benzene at 20℃; for 12h;
  • 34
  • [ 720-44-5 ]
  • [ 70-55-3 ]
  • [ 258277-16-6 ]
YieldReaction ConditionsOperation in experiment
97% With iodine In acetonitrile at 20℃; for 1h;
92% With perrhenic acid anhydride In dichloromethane at 20℃; for 1h;
85% With copper(II) bis(trifluoromethanesulfonate); 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane for 1h; Reflux; Inert atmosphere; Schlenk technique; 2.2. General procedure General procedure: The borrowing hydrogen process is achieved ina sealed Schlenk tube under argon atmosphere.Benzhydrol derivative (0.1 mmol), p-toluene sulfonamide(0.1 mmol), Cu(OTf)2 (5 mol%) anddppe (5 mol%) were dissolved in dried 1,4-dioxane(0.5 mL). The mixture was stirred for 1 h under reflux.After cooling to room temperature, the reaction mixturewas passed through a short silica column (eluentethyl acetate), and then the solvent was removedunder reduced pressure. The obtained residue waspurified by column chromatography (EtOAc-PE,1:10) to afford the diarylated amines.
82% In nitromethane for 1h; Heating;
80% With iron(III) chloride at 20℃; neat (no solvent);

  • 35
  • [ 720-44-5 ]
  • [ 2538-34-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 96 percent / H2SO4 / 17 h / 20 °C 2: 100 percent / H2O; LiOH / acetonitrile / 3 h / 50 °C
  • 36
  • [ 720-44-5 ]
  • [ 4578-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CHCl3 / 0.17 h 2: dimethylformamide / 3 h / 80 °C
Multi-step reaction with 2 steps 1: 99 percent / HCl gas / CaCl2 / benzene / 0.5 h 2: 75 percent / KCN / dibenzo-18-crown-6 / acetonitrile / 54 h / Heating
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 1.2: 8 h / 20 °C 2.1: iron(III) chloride / dichloromethane / 1.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 1.2: 8 h / 20 °C 2.1: iron(III) chloride / dichloromethane / 1.5 h / 20 °C

  • 37
  • [ 720-44-5 ]
  • [ 6853-54-9 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydrogen sulphite at 150℃; for 1h; Neat (no solvent);
94% With chloro-trimethyl-silane; bismuth sulphate at 20℃; for 8.5h;
83% With 2,3,3-trimethyl-1-(3-sulfonatopropyl)-3H-indolium In acetonitrile at 25℃; for 3h; Irradiation; Green chemistry;
70% With bismuth(III) chloride; chloro-trimethyl-silane In dichloromethane at 20℃; for 12h;
49% With pyridinium poly(hydrogen fluoride) In tetrahydrofuran at 20℃; Cooling with ice; 4.2. General procedure for the reaction of 1,1-diaryl methanols (1a-f) with PPHF General procedure: A solution of 1,1-diaryl methanol, 1a-f (0.2-1.0 g, 0.73-5.43 mmol) was taken in a plastic bottle (13.4 cm×5.6 cm) in dry THF. PPHF (1.5-3.0 mL) was added to the stirred solution at ice-cold temperature. The contents were further stirred for 6-24 h and the reaction mixture was quenched with liquor ammonia at ice-cold temperature. The organic compound was extracted with DCM, washed with Na2CO3 (10%) solution, water, brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford viscous oil, which was purified by flash column chromatography to give products 2a-e, 3a and 3b in varying yields of 33-72%.
Multi-step reaction with 2 steps 1: SOCl2; pyridine 2: diethyl ether; pyridine
Multi-step reaction with 2 steps 1: SOCl2; pyridine 2: diethyl ether; water
Multi-step reaction with 3 steps 1: pyridine 2: concentrated aqueous HCl / oder Acetylchlorid 3: diethyl ether; pyridine
Multi-step reaction with 3 steps 1: pyridine 2: concentrated aqueous HCl / oder Acetylchlorid 3: diethyl ether; water
Multi-step reaction with 3 steps 1: pyridine 2: concentrated aqueous HCl / oder Acetylchlorid 3: diethyl ether; pyridine
Multi-step reaction with 3 steps 1: pyridine 2: concentrated aqueous HCl / oder Acetylchlorid 3: diethyl ether; water
Multi-step reaction with 3 steps 1: pyridine 2: concentrated aqueous HCl 3: diethyl ether; pyridine
Multi-step reaction with 3 steps 1: pyridine 2: concentrated aqueous HCl 3: diethyl ether; water

  • 38
  • [ 720-44-5 ]
  • [ 98-88-4 ]
  • [ 138768-32-8 ]
YieldReaction ConditionsOperation in experiment
98% With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 75℃; for 5h;
  • 39
  • [ 720-44-5 ]
  • [ 75-36-5 ]
  • [ 5267-47-0 ]
YieldReaction ConditionsOperation in experiment
90% With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 75℃; for 9h;
  • 41
  • [ 720-44-5 ]
  • [ 100-47-0 ]
  • [ 138768-32-8 ]
YieldReaction ConditionsOperation in experiment
91% With water; tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 150℃; for 0.25h; Microwave irradiation; Green chemistry; General procedure: A mixture of alcohol (1.0 equiv), nitrile(2.0 equiv), water (2.0 equiv), Ca(OTf)2 (5 mol %), and additive-Bu4NPF6(5 mol %) was subjected to microwave irradiation for 15 min at 120 C. After the completion of the reaction (monitored by TLC), the reaction mixture was diluted with minimum amount of water and extracted into ethylacetate, combined organic layers were dried over anhydrous Na2SO4, solvent was removed under reduced pressure, and the crude reaction mass was purified by column chromatography on silica gel using ethylacetate and hexanes as the eluents to yield the amides. Spectral data of all the compounds were in agreement with the reported data. Spectral data of representative compounds.
79% With o-benzenedisulfonimide at 100℃; for 16h;
  • 42
  • [ 720-44-5 ]
  • [ 75-05-8 ]
  • [ 5267-47-0 ]
YieldReaction ConditionsOperation in experiment
86% With water; tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 120℃; for 0.25h; Microwave irradiation; Green chemistry; General procedure: A mixture of alcohol (1.0 equiv), nitrile(2.0 equiv), water (2.0 equiv), Ca(OTf)2 (5 mol %), and additive-Bu4NPF6(5 mol %) was subjected to microwave irradiation for 15 min at 120 C. After the completion of the reaction (monitored by TLC), the reaction mixture was diluted with minimum amount of water and extracted into ethylacetate, combined organic layers were dried over anhydrous Na2SO4, solvent was removed under reduced pressure, and the crude reaction mass was purified by column chromatography on silica gel using ethylacetate and hexanes as the eluents to yield the amides. Spectral data of all the compounds were in agreement with the reported data. Spectral data of representative compounds.
85% With o-benzenedisulfonimide for 5h; Reflux;
77% With [((CH3)5Cp)2Zr(H2O)2OSO2C8F17]+[OSO2C8F17]-*THF In neat (no solvent) at 80℃; for 8h;
  • 43
  • [ 1076-38-6 ]
  • [ 720-44-5 ]
  • [ 1198104-34-5 ]
YieldReaction ConditionsOperation in experiment
98% With 1-(4-sulfonylbutyl)pyridinium trifluoromethanesulfonate at 60℃; for 2h; Green chemistry;
97% With iodine In nitromethane at 50℃; for 4h;
  • 44
  • [ 720-44-5 ]
  • [ 536-74-3 ]
  • [ 120615-75-0 ]
YieldReaction ConditionsOperation in experiment
86% With 4-n-butyl-4-(3-sulfopropyl)thiomorpholinium 1,1-dioxide trifluoromethane sulfonate at 100℃; for 2h; Green chemistry;
84% With copper(II) bis(trifluoromethanesulfonate) In ethylene dibromide at 120℃; for 12h;
70% With indium(III) triflate In dichloromethane at 20 - 60℃; General Procedure for Indium(III)-catalyzed DirectCoupling of Alcohols with Terminal Alkynes General procedure: Alcohol (0.25 mmol) was added to a mixture of alkyne(0.5 mmol) and In(OTf)3 (0.05 mmol) in DCE (1 mL) atroom temperature under air. The reaction mixture was stirredat 60 °C for 12-24 h. After cooling down to room temperatureand concentrating in vacuum, the residue was purifiedby silica-gel flash column chromatography using petroleumether/EtOAc as the eluent to give the desired product.
54% With TfOH; iron(III) trifluoromethanesulfonate In DCE; N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux;

  • 45
  • [ 7294-51-1 ]
  • [ 100-52-7 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2,4,6-tris(4-methoxyphenyl)boroxine With bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; 4-chlorobenzophenone In tetrahydrofuran at 20℃; Stage #2: benzaldehyde In tetrahydrofuran at 20℃;
  • 46
  • [ 123-11-5 ]
  • [ 100-58-3 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 4-methoxy-benzaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water Schlenk technique; Inert atmosphere;
84% In diethyl ether at 0 - 20℃; Inert atmosphere; Reflux; General procedure from an aldehyde using phenylmagnesium bromide. General procedure: To an oven-dried, argon purged round bottom flask containing the aldehyde (1 mmol) in diethyl ether (2 mL) at 0 °C, was added phenylmagnesium bromide (0.5 mL, 1.5 mmol, 1.5 equiv., 3.0 M solution in diethyl ether) dropwise over 5 minutes. The reaction was then allowed to warm to room temperature and left to stir overnight.* Saturated aqueous solution of NH4Cl was then added slowly and stirred for a few minutes. Diethyl ether was then added and the layers were separated. The aqueous layer was extracted with diethyl ether (2 x) and then the combined organic extracts were washed with water and brine, then dried over MgSO4. Purification was performed by flash column chromatography on silica gel when needed. * Reaction was stirred overnight at reflux for the synthesis of 4-methoxy-α-phenylbenzenemethanol and 3-methoxy-α-phenylbenzenemethanol.
83% In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
78% In tetrahydrofuran at 0 - 20℃; for 2h; Schlenk technique; Inert atmosphere;
78% In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
54% In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;
In diethyl ether
In diethyl ether Reflux;
In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
In diethyl ether
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0 - 20 °C 1.2: 18 h / 20 °C 2.1: 9-BBN-2,6-lutidine borenium bistriflimide; triethylsilane / dichloromethane / 20 °C / Glovebox; Inert atmosphere; Sealed tube 2.2: 20 °C
In tetrahydrofuran at 0 - 20℃;
In diethyl ether at 0℃; for 1h;
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference: [1]Rackl, Daniel; Kais, Viktor; Kreitmeier, Peter; Reiser, Oliver [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2157 - 2165]
[2]Lebleu, Thomas; Paquin, Jean-François [Tetrahedron Letters, 2017, vol. 58, # 5, p. 442 - 444]
[3]Xu, Xiao-Long; Li, Zhi [Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8196 - 8200][Angew. Chem., 2017, vol. 129, # 28, p. 8308 - 8312]
[4]Jaimes, Maria Camila Blanco; Ahrens, Alexander; Pflästerer, Daniel; Rudolph, Matthias; Hashmi, A. Stephen K. [Chemistry - A European Journal, 2015, vol. 21, # 1, p. 427 - 433]
[5]Balakrishnan, Venkadesh; Murugesan, Vetrivelan; Chindan, Bincy; Rasappan, Ramesh [Organic Letters, 2021, vol. 23, # 4, p. 1333 - 1338]
[6]Lielpetere, Anna; Jirgensons, Aigars [Organic and Biomolecular Chemistry, 2018, vol. 16, # 28, p. 5094 - 5096]
[7]Zhang, Jintang; Wang, Zhentao; Wang, Ye; Wan, Changfeng; Zheng, Xiaoqi; Wang, Zhiyong [Green Chemistry, 2009, vol. 11, # 12, p. 1973 - 1978]
[8]Location in patent: scheme or table Pajouhesh, Hassan; Feng, Zhong-Ping; Ding, Yanbing; Zhang, Lingyun; Pajouhesh, Hossein; Morrison, Jerrie-Lynn; Belardetti, Francesco; Tringham, Elizabeth; Simonson, Eric; Vanderah, Todd W.; Porreca, Frank; Zamponi, Gerald W.; Mitscher, Lester A.; Snutch, Terrance P. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1378 - 1383]
[9]Greene, Margaret A.; Yonova, Ivelina M.; Williams, Florence J.; Jarvo, Elizabeth R. [Organic Letters, 2012, vol. 14, # 16, p. 4293 - 4296]
[10]Meng, Li; Su, Jihu; Zha, Zhenggen; Zhang, Li; Zhang, Zhenlei; Wang, Zhiyong [Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545]
[11]Denmark, Scott E.; Ueki, Yusuke [Organometallics, 2013, vol. 32, # 22, p. 6631 - 6634]
[12]Zheng, Lewei; Huang, Hongli; Yang, Chao; Xia, Wujiong [Organic Letters, 2015, vol. 17, # 4, p. 1034 - 1037]
[13]Chebolu, Rajesh; Bahuguna, Ashish; Sharma, Reena; Mishra, Vivek Kumar; Ravikumar [Chemical Communications, 2015, vol. 51, # 84, p. 15438 - 15441]
[14]Maiti, Debabrata; Halder, Atreyee; De Sarkar, Suman [Advanced Synthesis and Catalysis, 2019, vol. 361, # 21, p. 4941 - 4948]
  • 47
  • [ 4648-54-8 ]
  • [ 720-44-5 ]
  • [ 57272-10-3 ]
YieldReaction ConditionsOperation in experiment
98% With indium tribromide In dichloromethane at 20℃; for 0.0833333h; 2 4.7 General procedure for the preparation of 1-azido-1,1-diaryl methane General procedure: A solution of 1,1-diarylmethanol, 1r-w (200mg, 0.80-1.08mmol) in dry CH2Cl2 (5mL) and TMSN3 (1.5equiv) were placed in a 25mL round-bottom flask fitted with guard tube. InBr3 (2mol%) was added to this reaction mixture. The contents were stirred at room temperature and the progress of reaction was monitored by TLC analyses. After stirring the contents for appropriate time period, the reaction was quenched with water. The product was extracted with CH2Cl2 (3×15mL), washed with 10% Na2CO3 (20mL), water (20mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to give brownish oil. Purification by flash chromatography afforded the products 2r-w.
90% With tin(IV) chloride In dichloromethane at 20℃; for 10h;
  • 48
  • [ 720-44-5 ]
  • [ 74-88-4 ]
  • [ 7364-21-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 8h; Inert atmosphere;
Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 8h; B. General Procedure for the Synthesis of Starting Materials1 General procedure: To a stirred solution of alcohol (0.0123 mol) in anhydrous THF (30 mL) was added sodium hydride (60 percent in oil, 2 equiv, 0.0246 mol) partially at 0 °C . The mixture was further stirred at 0 °C for 1h before slowly addition of MeI (1.5 equiv). After stirred at room temperature for 8h, the reaction was quenched by addition of ice-water and extracted with EtOAc twice. The combined organic phase was washed with brine and dried over MgSO4. Evaporation of solvent provided the crude product as a color residue. The crude product was purified by column chromatography on silica gel (petroleum ether /ethyl acetate = 20 : 1) to afford ethers 1a-p.
Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 8h; General Procedure for the Synthesis of Starting Materials General procedure: To a stirred solution of alcohol (0.0123 mol) in anhydrous THF (30 mL) was added sodium hydride (60 percent in oil, 2 equiv, 0.0246 mol) partially at 0 °C . The mixture was further stirred at 0 °C for 1h before slowly addition of MeI (1.5 equiv). After stirred at room temperature for 8h, the reaction was quenched by addition of ice-water and extracted with EtOAc twice. The combined organic phase was washed with brine and dried over MgSO4. Evaporation of solvent provided the crude product as a color residue. The crude product was purified by column chromatography on silica gel (petroleum ether /ethyl acetate = 20 : 1) to afford ethers 1a-p.

  • 49
  • [ 720-44-5 ]
  • [ 36635-61-7 ]
  • p-methoxyphenyl(phenyl)methyl p-tolyl sulfone [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With water at 80℃; for 2h; General procedure for the synthesis of [E]- and [Z]-allyl sulfones (6) and benzyl sulfones (7) General procedure: A stirred solution of p-toluenesulfonylmethyl isocyanide (TosMIC) (1.1 mmol) and alcohols 2 or 3 (1 mmol) in 1 mL of [Hmim]HSO4-H2O (10:1) was heated at 80 °C for 2-14 h (Table 2). The reaction progress was monitored by TLC. Upon completion, the reaction mixture was cooled to rt and extracted with dichloromethane (3 × 10 mL). The combined organic phase was dried over MgSO4, filtered and evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a gradient mixture of hexane/ethyl acetate (8:2) as eluent to give the corresponding pure sulfone derivatives 6 and 7. All the products are known compounds15(c), 15(e) and 16(c) and were characterized by comparison of their mp and spectral data with those of reported in the literature. After isolation of the product, the remaining mother liquid containing the ionic liquid was washed with dichloromethane (2 × 5 mL) to remove any organic impurity, dried under vacuum at 90 °C to afford [Hmim]HSO4 in an excellent yield (96%), which was used in subsequent runs without further purification (Fig. 1). The recovery yield of [Hmim]HSO4 in subsequent runs was >93%.
  • 50
  • [ 720-44-5 ]
  • [ 536-74-3 ]
  • [ 1353312-41-0 ]
  • (Z)-(1-iodo-3-(4-methoxyphenyl)prop-1-ene-1,3-diyl)dibenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine; iron; sodium iodide In ethylene dibromide at 55℃; optical yield given as %de; 2. General Procedure for the Synthesis of Alkenyl iodides General procedure: To a stirred solution of iron powder (0.5 mmol), iodine (0.5 mmol), sodium iodide (1.0 mmol) and alcohol (0.5 mmol) in DBE (1.0 mL) was added alkyne (1.5 mmol). The mixture was heated at 55°C and stirred for 8-12 h. Upon completion of the reaction, the mixture was filtered through a short column of silica gel and washed with ethyl acetate, and the solvents were removed by rotary evaporation to provide raw product. Then the product was purified on silica gel to afford the desired product.
  • 51
  • [ 108-86-1 ]
  • [ 123-11-5 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: bromobenzene With iodine; magnesium In diethyl ether at 20℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In diethyl ether Sealed tube; Inert atmosphere;
96% Stage #1: bromobenzene With magnesium In tetrahydrofuran; ethylene dibromide at 20℃; for 1h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; ethylene dibromide at 20℃; Inert atmosphere;
69% With 1,10-Phenanthroline; 3-chloroprop-1-ene; trifluoroacetic acid; cobalt(II) bromide; zinc In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube;
Stage #1: bromobenzene With magnesium Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde Inert atmosphere;

  • 52
  • [ 108-22-5 ]
  • [ 720-44-5 ]
  • [ 807631-95-4 ]
  • [ 807631-96-5 ]
YieldReaction ConditionsOperation in experiment
With Candida antarctica lipase B W104A In toluene at 70℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; 4.4. General procedure for the kinetic resolution of diarylmethanols General procedure: Diarylmethanol (0.25 mmol), isopropenyl acetate (0.38 mmol, 41 μl) and CALB W104A (45 mg) were mixed in toluene (1 mL) and stirred at 70 °C for 6-24 h. The conversion was determined by 1H NMR. The enantiomeric excess (ee) of the products, and in some cases also of the remaining substrates were determined by chiral HPLC. E values were calculated from eep and conversion unless otherwise noted.25
  • 53
  • [ 720-44-5 ]
  • [ 2251-50-5 ]
  • [ 1401963-00-5 ]
YieldReaction ConditionsOperation in experiment
71% With pyridine In benzene at 20℃; for 12h; Inert atmosphere;
  • 54
  • [ 79538-29-7 ]
  • [ 720-44-5 ]
  • [ 1401963-05-0 ]
YieldReaction ConditionsOperation in experiment
71.2% With pyridine In benzene at 20℃; for 12h; Inert atmosphere;
  • 55
  • [ 720-44-5 ]
  • [ 121-90-4 ]
  • [ 95702-25-3 ]
YieldReaction ConditionsOperation in experiment
72.8% With pyridine In benzene at 20℃; Inert atmosphere;
  • 56
  • [ 720-44-5 ]
  • [ 6238-34-2 ]
  • [ 1404054-99-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; for 96h; 35 1. Preparation of (4-methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate (Compound 73). Quinuclidine-3-carboxylic acid hydrochloride (150 mg, 0.78 mmol), EDC (225 mg, 1.17 mmol), and HOBT (180 mg, 1.17 mmol) were dissolved in dry THF (7.5 ml). (4-Methoxyphenyl)(phenyl)methanol (184 mg, 0.86 mmol) and TEA (382 μl, 2.74 mmol) were added, and the resulting reaction was stirred at room temperature for four days. THF was removed under vacuum, and the crude residue was partitioned between EtOAc and water. The organic phase was washed with a sat. NaHCO3, dried over Na2SO4, filtered, and evaporated. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to EtOAc/MeOH=7:3+1% NH4OH) to give (4-methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate (37 mg, mixture of diastereoisomers). The compound was used as such in the next step.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; for 96h; 35.1 1- Preparation of (4-methoxyphenyl)(phenyl)methyl quinuclidine-3- carboxylate (compound 73)Quinuclidine-3-carboxylic acid hydrochloride (150 mg, 0.78 mmol), EDC (225 mg, 1.17 mmol) and HOBT (180 mg, 1.17 mmol) were dissolved in dry THF (7.5 ml). (4-Methoxyphenyl)(phenyl)methanol (184 mg, 0.86 mmol) and TEA (382 μ, 2.74 mmol) were added, and the resulting reaction was stirred at room temperature for four days. THF was removed under vacuum, and the crude residue was partitioned between EtOAc and water. The organic phase was washed with a sat. NaHCO3, dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to EtOAc/MeOH=7:3 + 1% NH4OH) to give (4-methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate (37 mg, mixture of diastereoisomers). The compound was used as such in the next step.
  • 57
  • [ 100-52-7 ]
  • [ 100-66-3 ]
  • [ 720-44-5 ]
  • [ 7500-76-7 ]
YieldReaction ConditionsOperation in experiment
1: 58% 2: 14% Stage #1: benzaldehyde With pyridine; aluminium bromide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: methoxybenzene In dichloromethane at 20℃; for 24.5h; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In dichloromethane for 0.0833333h;
1: 58% 2: 14% Stage #1: benzaldehyde With pyridine; aluminum tri-bromide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: methoxybenzene In dichloromethane at 20℃; for 24h; Inert atmosphere;
1: 34% 2: 22% Stage #1: benzaldehyde With pyridine; aluminum tri-bromide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: methoxybenzene In dichloromethane at 20℃; for 24h; Inert atmosphere;
  • 58
  • [ 720-44-5 ]
  • [ 98-83-9 ]
  • [ 1446744-01-9 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydrogen sulfate; silica gel In 1,2-dichloro-ethane at 60℃; for 4h;
73% With 4H(1+)*O40SiW12(4-)*C5H9NO In 1,2-dichloro-ethane at 80℃; for 2h; 2.3. Typical procedure for direct dehydrative coupling of alcohols with alcohols General procedure: To a 4 mL reaction vial, diphenylmethanol (0.6 mmol), α-phenethylalcohol (1.2 mmol), [NMPH]H3[SiW12O40] (4 mol%) and 1,2-dichloroethane(3 mL) were added. Then the reaction was carried out inscrew cap vials with a Teflon seal at 80 °C for desired time. After cooling to room temperature, the mixture was further purified by column chromatography (petroleum ether/EtOAc) to afford the desired products.
  • 59
  • [ 359-06-8 ]
  • [ 720-44-5 ]
  • [ 1580541-35-0 ]
YieldReaction ConditionsOperation in experiment
83.3% With pyridine In benzene at 20℃; for 12h; Inert atmosphere;
  • 60
  • [ 720-44-5 ]
  • [ 541-88-8 ]
  • [ 1580541-39-4 ]
YieldReaction ConditionsOperation in experiment
86.6% With pyridine In benzene at 20℃; for 12h; Inert atmosphere;
  • 61
  • [ 79-36-7 ]
  • [ 720-44-5 ]
  • [ 1580541-49-6 ]
YieldReaction ConditionsOperation in experiment
81.6% With pyridine In benzene at 20℃; for 12h; Inert atmosphere;
  • 62
  • [ 720-44-5 ]
  • [ 120-46-7 ]
  • [ 954374-32-4 ]
YieldReaction ConditionsOperation in experiment
100% In 1,1,2,2-tetrachloroethane for 36h; Reflux;
87% In dichloromethane at 60℃; for 4h; Sealed tube; 4.2.4 2-( (4-Methoxyphenyl) (phenyl)methyl-1,3-diphenylpropane-1,3-dione (7) General procedure: 4.1.2 Typical procedure for direct benzylation of 1,3-dicarbonyl derivatives using alcohols as alkylating agents catalyzed by 1a: To a 10mL sealed tube was added dibenzoylmethane (112 mg, 0.5 mmol), benzhydrol (101 mg, 0.55 mmol), CH2Cl2 (2 mL) and catalyst (39.8 mg, 5 mol%). The mixture was stirred at 60 °C for 4 h. Then the reaction mixture was evaporated in vacuum, CH2Cl2 (3×10 ml) was added to the reaction mixture and the catalyst was filtered for the next cycle of reaction. The combined CH2Cl2 solution was removed by evaporation in vacuum and was then subject to silica gel column chromatograph; the product (4) was obtained: 185 mg, isolated yield 95 %
83% With [n-BuCpZr(OH2)3]22-OH)2(OSO2C8F17)4*6H2O In dichloromethane at 60℃; for 4h; Inert atmosphere; Sealed tube; Typical procedure for the direct alkylation of 1,3-dicarbonyl derivatives withbenzhydrylic alcohols catalyzed by complex 2a·6H2O General procedure: To a 10 mL sealed tube was added dibenzoylmethane (112 mg, 0.5 mmol), benzhydrol (101mg, 0.55 mmol), CH2Cl2(2 mL) and catalyst (33.5 mg, 2.5 mol %). The mixture was stirred at 60 oC for 4 hours. After evaporation in vacuum and subject to silica gel column chromatograph, product 6a was obtained: 175 mg ,isolated yield 90%.
  • 63
  • [ 26546-24-7 ]
  • [ 5908-41-8 ]
  • [ 720-44-5 ]
YieldReaction ConditionsOperation in experiment
61% With chloro(1,5-cyclooctadiene)rhodium(I) dimer In ethanol at 80℃; for 12h; Schlenk technique; Inert atmosphere; Table 1, Entry 1 General procedure: A Schlenk tube was charged with NaBPh4 (2a, 51.5 mg, 0.150 mmol) and [Rh(OH)(cod)]2 (1.4 mg, 3.1 µmol, 6 mol% Rh). The tube was evacuated and backfilled with nitrogen, and then benzoyltrimethylsilane (1a, 17.9 mg, 0.100 mmol) and toluene (1.0 mL) were added via syringe through the septum. The mixture was heated at 90 °C for 8 h. The reaction mixture was filtered through a plug of Florisil washing with hexane-AcOEt (5:1), and the filtrate was concentrated. Purification by preparative TLC on silica gel (hexane:AcOEt = 8:1) afforded the title compound (3aa, 17.6 mg, 0.069 mmol, 68%) as a pale yellow oil.
  • 64
  • [ 720-44-5 ]
  • [ 536-74-3 ]
  • [ 1616471-08-9 ]
  • [ 1616471-09-0 ]
YieldReaction ConditionsOperation in experiment
80 % de With tetrafluoroboric acid In ethylene dibromide at 55℃; Overall yield = 38 %; 2. General Procedure for the Synthesis of fluoroalkenes General procedure: To a stirred solution of alcohol (0.5 mmol) andfluoroboric acid (0.75mmol)in DBE (2.0 mL) was added alkyne (0.6 mmol). The mixture was heated at 55°C andstirred for 8-10 h. Upon completion of the reaction, the solvent was removed by rotary evaporation to provide rawproduct, which waspurified on silica gel to afford themixture of E/Z isomers.
  • 65
  • [ 100-42-5 ]
  • [ 720-44-5 ]
  • [ 1143572-90-0 ]
YieldReaction ConditionsOperation in experiment
89% With 1-methyl-2-oxopyrrolidinium hydrogen sulfate In neat (no solvent) at 80℃; for 6h; Sealed tube; Green chemistry;
86% With silica-supported policresulen In ethylene dibromide at 80℃; for 15h; SiO2/policresulen composite catalyzed β-alkylation of styrene with benzhydrol. General procedure: All reactions were conducted in a 10-mLV-type vessel equipped with a triangular magnetic stirrer. In atypical reaction, benzhydrol (92.1 mg, 0.5 mmol), styrene (62.4mg, 0.6 mmol), and 1b (20 mg, 2 mol%) were mixed in1,2-dibromoethane (1.0 mL) and stirred for 5 h at 80 °C. Afterthe reaction, the mixture was cooled to room temperature andpetroleum ether (3.0 mL) was added prior to centrifugation.The liquid phase was subjected to isolation with PTLC (PE aseluent). The desired product, 4a, was obtained in a yield of92%. As for the solid phase, after washing with PE (3.0 mL × 3)and drying under vacuum, 1b was used in the next run with asimilar procedure. Tests of the substrate scope were conductedin the same manner.
78% With 10% Moβ zeolite In neat (no solvent) at 70℃; for 3h; Sealed tube; 2.2. Experimental procedure General procedure: 10% Moβ zeolite (100 mg) was introduced to the well stirred solution of vinylarene (1 mmol) and alcohol (0.8 mmol) in a 15 ml of sealed vial and the reaction mixture was allowed to stir at 70 °C. After disappearance of the substrate (monitored by TLC) or after an appropriate time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate. The catalyst was removed by filtration, rinsed with ethyl acetate and removal of solvent in vacuo yielded a crude residue. The crude residue was further purified by column chromatography on silica gel (230-400 mesh) using ethyl acetate/hexane as eluent to afford pure products. All the products were identified on the basis of NMR spectral data and quantified using gas chromatography. More details on catalyst characterization and analytical procedures are provided in supporting information.
  • 66
  • [ 720-44-5 ]
  • [ 785-56-8 ]
  • (4-methoxyphenyl)(phenyl)methyl 3,5-bis(trifluoromethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; triethylamine In dichloromethane at 0 - 20℃; Schlenk technique; General procedure for the synthesis of benzoate estersvia the acid chloride (GPI) General procedure: A 50 mL Schlenk flask equipped with a magnetic stir bar was charged with an alcohol (5.00mmol, 1.00 equiv.), 4-DMAP (31 mg, 0.25 mmol, 0.05 equiv.), Et3N (5.0 ml, 3.5 g, 35 mmol,7.0 equiv.), and DCM (50 mL). The mixture was cooled to 0 °C, then (trifluoromethyl)benzoylchloride45 (5.50 mmol, 1.10 equiv.) was added dropwise. The reaction mixture was allowed towarm to room temperature, solvent was evaporated under reduced pressure and the residuewas purified by flash chromatography.
  • 67
  • [ 17814-72-1 ]
  • [ 720-44-5 ]
  • (4-methoxyphenyl)(phenyl)methyl hex-3-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 3h; Schlenk technique; Inert atmosphere;
  • 68
  • [ 720-44-5 ]
  • [ 93-91-4 ]
  • 2-((4-methoxyphenyl)(phenyl)methyl)-1-phenylbutane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 60℃; for 4h; Sealed tube; 4.2.20 2-( (4-Methoxyphenyl) (phenyl)methyl-1-phenylbutane-1,3-dione (23) General procedure: 4.1.2 Typical procedure for direct benzylation of 1,3-dicarbonyl derivatives using alcohols as alkylating agents catalyzed by 1a: To a 10mL sealed tube was added dibenzoylmethane (112 mg, 0.5 mmol), benzhydrol (101 mg, 0.55 mmol), CH2Cl2 (2 mL) and catalyst (39.8 mg, 5 mol%). The mixture was stirred at 60 °C for 4 h. Then the reaction mixture was evaporated in vacuum, CH2Cl2 (3×10 ml) was added to the reaction mixture and the catalyst was filtered for the next cycle of reaction. The combined CH2Cl2 solution was removed by evaporation in vacuum and was then subject to silica gel column chromatograph; the product (4) was obtained: 185 mg, isolated yield 95 %
  • 69
  • [ 720-44-5 ]
  • [ 106-96-7 ]
  • [ 1561042-18-9 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 0 - 20℃; for 0.833333h; Stage #2: propargyl bromide In water; toluene at 0℃; for 3h;
  • 70
  • [ 16717-64-9 ]
  • [ 720-44-5 ]
  • [ 51527-49-2 ]
YieldReaction ConditionsOperation in experiment
83% With bis(trifluoromethanesulfonyl)amide In 1,2-dichloro-ethane at 40℃; for 0.333333h; Inert atmosphere;
  • 71
  • [ 720-44-5 ]
  • [ 545-06-2 ]
  • (4-methoxyphenyl)(phenyl)methyl 2,2,2-trichloroacetimidate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; Inert atmosphere;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; 4.2. General procedure of trichloroacetimidate formation General procedure: Trichloroacetonitrile (1.1 mL,10.8 mmol, 3.0 equiv)was added toa solution of a-methyl-2-naphthalenemethanol (0.62 g, 3.6 mmol,1.0 equiv) in CH2Cl2 (7.2 mL) at 0 C in an oven-dried Schlenk flask.After the solution had been stirring for 5 min, DBU (0.27 mL,0.25 mmol, 0.5 equiv) was then added dropwise. The resultingmixture was allowed to warm slowly to room temperature overnight.Upon completion, the reaction mixture was concentrated invacuo and loaded directly onto a RediSep load cartridge containingpre-equilibrated and dried silica. Purification by silica gel flashcolumn chromatography (pre-equilibrated 10 g RediSep column,10% ethyl acetate/hexane3% triethylamine) resulted in 4a (0.93 g,82%) as a white solid.
  • 72
  • [ 720-44-5 ]
  • [ 614-20-0 ]
  • 3-(4-methoxyphenyl)-1,3-diphenyl-1-propanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With iodine In nitromethane at 70℃; for 2h; Schlenk technique;
73% Stage #1: 1-(4-methoxyphenyl)-1-phenylmethanol With pentafluorophenylboronic acid; oxalic acid In nitromethane at 20℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: 3-oxo-3-phenylpropionic acid In nitromethane at 50℃; for 27h; Inert atmosphere; Glovebox;
  • 73
  • [ 720-44-5 ]
  • [ 13422-77-0 ]
  • [ 186083-47-6 ]
YieldReaction ConditionsOperation in experiment
92% With iodine In nitromethane at 70℃; for 6h; Schlenk technique;
  • 74
  • 3-(3-methoxy-phenyl)-3-oxo-propionic acid [ No CAS ]
  • [ 720-44-5 ]
  • 1-(3-methoxyphenyl)-3-(4-methoxyphenyl)-3-phenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With iodine In nitromethane at 70℃; for 6h; Schlenk technique;
  • 75
  • [ 720-44-5 ]
  • [ 40009-78-7 ]
  • 3-(4-methoxyphenyl)-3-phenyl-1-(o-tolyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With iodine In nitromethane at 70℃; for 6h; Schlenk technique;
  • 76
  • 3-(naphthalen-2-yl)-3-oxopropanoic acid [ No CAS ]
  • [ 720-44-5 ]
  • [ 1613458-40-4 ]
YieldReaction ConditionsOperation in experiment
91% With iodine In nitromethane at 70℃; for 6h; Schlenk technique;
  • 77
  • [ 541-50-4 ]
  • [ 720-44-5 ]
  • [ 76217-07-7 ]
YieldReaction ConditionsOperation in experiment
87% With iodine In nitromethane at 70℃; for 6h; Schlenk technique;
  • 78
  • [ 720-44-5 ]
  • [ 147-93-3 ]
  • 2-[(4-methoxyphenyl)(phenyl)methyl]thio}benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With sodium tetrachloroaurate(III) dihydrate In water at 120℃; for 16h; Sealed tube;
75% With dichloro bis(acetonitrile) palladium(II) In water at 120℃; for 16h; Sealed tube;
  • 79
  • [ 37510-42-2 ]
  • [ 720-44-5 ]
  • S-ethyl 2-benzoyl-3-(4-methoxyphenyl)-3-phenylpropanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With iron(III) chloride hexahydrate In acetonitrile at 25℃; for 24h; Typical Procedure for the Preparation of α-Alkylated β-OxoThioester 3 General procedure: The mixture of α-oxo ketene dithioacetals 1 (0.25 mmol), alcohols 2 (0.25 mmol), and FeCl3·6H2O (20 mg, 0.075 mmol) in MeCN (1 mL) was stirred for 10 h at r.t. Another 0.125 mmol of alcohols was then added, and the mixture was further stirred for 14 h at r.t. until 1 was completely consumed by TLC monitoring.The reaction mixture was then added to cold water (50 mL),and desired products 3 as a solid deposited from the reaction system. After filtered, the crude product 3 was purified by flash silica gel chromatography [PE (60-90 °C)-EtOAc, 15:1 v/v] togive pure 3 in good yield.
  • 80
  • [ 720-44-5 ]
  • [ 540-51-2 ]
  • [ 93017-90-4 ]
YieldReaction ConditionsOperation in experiment
93% With sulfuric acid In toluene at 20 - 60℃; for 3.5h; Inert atmosphere; 1.1.4. ((2-bromoethoxy)(phenyl)methyl)-benzene (6a). General procedure: To a mixture of 2-bromoethanol (0.79 mL, 8.03 mmoL), dry toluene (7 mL) and Conc. H2SO4 (1 mL), under air-tight nitrogen atmosphere, was dropwise added benzhydrol (5a; 1 g, 5.43 mmoL) in dry toluene (7 mL). After being stirred for 30 min at room temperature and 3 h at 60 °C, the reaction mixture was cooled, diluted with EtOAc (2x) and washed sequentially with water and saturated aqueous NaCl. The organic layer was dried over MgSO4 and distilled off in vacuo. The residue was purified by flash column chromatography (100 % n-hexanes to n-hexane/EtOAc; 97:3 stepwise gradient) to afford 18a as translucent oil which solidified gradually (1.47 g). Yield: 93 %; mp: 65-67 °C; 1H-NMR (300 MHz, CDCl3): δ 3.54 (t, J = 6.23 Hz, 2H), 3.81 (t, J = 6.23 Hz, 2H), 5.46 (s, 1H), 7.21-7.46 (m, 10H); MS (EI+) m/z: 290 [M+], 292 [M+2] showing relative intensity ratio ~ 1:1.
  • 81
  • [ 720-44-5 ]
  • [ 100-53-8 ]
  • benzyl ((4-methoxyphenyl)(phenyl)methyl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With toluene-4-sulfonic acid In acetonitrile for 12h; Reflux;
71% With N-cetyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 0.25h; Schlenk technique;
  • 82
  • [ 720-44-5 ]
  • [ 529-33-9 ]
  • C24H22O [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With 4H(1+)*O40SiW12(4-)*C5H9NO In 1,2-dichloro-ethane at 80℃; for 1.5h; 2.3. Typical procedure for direct dehydrative coupling of alcohols with alcohols General procedure: To a 4 mL reaction vial, diphenylmethanol (0.6 mmol), α-phenethylalcohol (1.2 mmol), [NMPH]H3[SiW12O40] (4 mol%) and 1,2-dichloroethane(3 mL) were added. Then the reaction was carried out inscrew cap vials with a Teflon seal at 80 °C for desired time. After cooling to room temperature, the mixture was further purified by column chromatography (petroleum ether/EtOAc) to afford the desired products.
  • 83
  • [ 1073-67-2 ]
  • [ 720-44-5 ]
  • C22H19ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 4H(1+)*O40SiW12(4-)*C5H9NO In 1,2-dichloro-ethane at 80℃; for 2h; 2.3. Typical procedure for direct dehydrative coupling of alcohols with alcohols General procedure: To a 4 mL reaction vial, diphenylmethanol (0.6 mmol), α-phenethylalcohol (1.2 mmol), [NMPH]H3[SiW12O40] (4 mol%) and 1,2-dichloroethane(3 mL) were added. Then the reaction was carried out inscrew cap vials with a Teflon seal at 80 °C for desired time. After cooling to room temperature, the mixture was further purified by column chromatography (petroleum ether/EtOAc) to afford the desired products.
  • 84
  • [ 720-44-5 ]
  • [ 1592-20-7 ]
  • C23H21ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With 4H(1+)*O40SiW12(4-)*C5H9NO In 1,2-dichloro-ethane at 80℃; for 2h; 2.3. Typical procedure for direct dehydrative coupling of alcohols with alcohols General procedure: To a 4 mL reaction vial, diphenylmethanol (0.6 mmol), α-phenethylalcohol (1.2 mmol), [NMPH]H3[SiW12O40] (4 mol%) and 1,2-dichloroethane(3 mL) were added. Then the reaction was carried out inscrew cap vials with a Teflon seal at 80 °C for desired time. After cooling to room temperature, the mixture was further purified by column chromatography (petroleum ether/EtOAc) to afford the desired products.
  • 85
  • [ 2885-00-9 ]
  • [ 720-44-5 ]
  • ((4-methoxyphenyl)(phenyl)methyl)(octadecyl)sulfane [ No CAS ]
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