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[ CAS No. 637-50-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 637-50-3
Chemical Structure| 637-50-3
Chemical Structure| 637-50-3
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Product Details of [ 637-50-3 ]

CAS No. :637-50-3 MDL No. :MFCD00009280
Formula : C9H10 Boiling Point : -
Linear Structure Formula :- InChI Key :QROGIFZRVHSFLM-QHHAFSJGSA-N
M.W : 118.18 Pubchem ID :252325
Synonyms :

Calculated chemistry of [ 637-50-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.34
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 3.35
Log Po/w (WLOGP) : 2.61
Log Po/w (MLOGP) : 4.08
Log Po/w (SILICOS-IT) : 2.82
Consensus Log Po/w : 3.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.0916 mg/ml ; 0.000775 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.111 mg/ml ; 0.000939 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.82
Solubility : 0.178 mg/ml ; 0.00151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 637-50-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P264-P303+P361+P353-P370+P378-P403+P235 UN#:3295
Hazard Statements:H225-H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 637-50-3 ]

* 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 [ 637-50-3 ]

[ 637-50-3 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 50-00-0 ]
  • [ 637-50-3 ]
  • [ 5663-20-7 ]
YieldReaction ConditionsOperation in experiment
95% In 1,4-dioxane at 60℃; for 5h;
89% With sulfuric acid; silica gel In water at 90℃; for 12h;
88% With 2,6-di-tert-butylphenoxy(difluoro)borane In 1,4-dioxane Heating;
80% With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate at 60 - 70℃; for 12h; Schlenk technique; Green chemistry; Typical Procedure for the Synthesis of 1,3-Dioxanes General procedure: In a typical experiment, styrene (10.0 mmol) and formaldehyde (20.0 mmol)were added successively into an oven-dried Schlenk tube. Upon efficient magneticstirring (for 10-20 min) the reaction mixture was then charged with bmimOTf (2-3 mL). The reaction mixture was stirred at 60-70 C and the progress of the reactionwas monitored by TLC and GC-MS (Table 2). After the completion of the reaction(TLC and GC-MS), the mixture was cooled to room temperature and the productwas extracted in dichloromethane (DCM). The pure product was obtained bycolumn chromatography (80:20 hexane-ethyl acetate mixture) and was fully characterizedby GC-MS, 1H NMR, 13C NMR, and elemental analysis. The spectral datawere found to be in agreement with the reported values.[20] The ionic liquid left afterthe extraction of product was dried and reused again.
With sulfuric acid; water

  • 3
  • [ 637-50-3 ]
  • [ 1196-45-8 ]
YieldReaction ConditionsOperation in experiment
90% With ammonium cerium(IV) nitrate; potassium bromide In dichloromethane; water at 20℃; for 0.5h;
85% With sulfuric acid; sodium bromide In chloroform; water at 30℃; Electrochemical reaction; Green chemistry; regioselective reaction; Procedure for synthesis of 1,2-dibromo-1-phenylethane General procedure: A solution of styrene (1.04 g, 10 mmol) in 25 ml CHCl3 was taken in a beaker-type glass-jacketed undivided cell (100 ml capacity) equipped with magnetic stirrer. To this solution, 30 ml of 25% NaBr solution (w/v) containing 2.45 g H2SO4 (25 mmol) was added. Two platinum foilel ectrodesofactive area 7.5 cm2 (3 cm x 2.5 cm) were placed carefully in the upper aqueous phase without touching the organic phase (Fig. 4). The inter electrode distance was maintained at 1 cm. The electrolysis was conducted galvanostatically at a current density of 40 mA/cm2 and the charge corresponding to 2 Faraday was passed. The organic phase was stirred with a magnetic stirrer at a rate of 40 rpm in such a way that the organic phase does not touch the electrodes. During the course of the reaction the cell voltage was measured to be 1.1-1.3 V. The electrolysis was continued until the reaction proceeded to completion. The progress of the reaction was monitored by high-performance liquid chromatography (HPLC, Shimadzu) using a Shimpack ODS-18 column (250 x 5 mm) as the stationary phase. The eluent consisted of 70:30 methanol/water. A flow rate of 1 ml per minute was employed. The samples were analyzed using an ultraviolet (UV) detector at a wavelength of 254 nm. After the completion of electrolysis, the lower organic phase was carefully separated from the reaction mixture. The aqueous portion was saved for reuse after extraction with CHCl3 (225 ml). The combined organic phase was washed with water, dried over anhydrous sodium sulfate, and distilled the solvent to get the product.
81% With potassium permanganate; hydrogen bromide In acetonitrile
With bromine In methanol at 25℃;
With bromine
With chloroform; bromine
With diethyl ether; bromine
With tetrachloromethane; bromine; acetic acid

  • 4
  • [ 637-50-3 ]
  • [ 4962-45-2 ]
YieldReaction ConditionsOperation in experiment
With bromine
With N-Bromosuccinimide; water In acetone at 20℃; Inert atmosphere; General Procedure A: Preparation of Bromohydrins 4a-4k1 General procedure: To a solution of olefin (5 mmol) and water (5 mL) in acetone (20 ml), NBS (5.50 mmol) was added and the mixture was stirred at room temperature. After completion of the reaction as indicated by TLC the mixture was concentrated in vaco and extracted with EtOAc-H2O (1:1) (3×10 mL). The organic portion was concentrated and the residue was purified by crystallization or column chromatography.
With N-Bromosuccinimide; ammonium acetate; water In acetone at 20℃; for 1h;
With N-Bromosuccinimide; sodium hydrogencarbonate In water; acetone at 20℃; for 2h;

  • 5
  • [ 93-54-9 ]
  • [ 637-50-3 ]
YieldReaction ConditionsOperation in experiment
97% With aluminum (III) chloride; triphenylphosphine In nitromethane at 80℃; for 2h; 2.2. A typical alcohol dehydration procedure General procedure: In a typical reaction, alcohol (0.4 mmol) was mixed with AlCl3 (0.02 mmol, 5 mol%) and triphenylphosphine (PPh3, 0.02 mmol, 5 mol%) in nitromethane (1.0 mL). Thereafter the mixture was stirred at 80 °C for 2 h. After the reaction, the mixture was cooled to room temperature, and the product was isolated using preparative thin layer chromatography (TLC, eluting solution: petroleum ether/ethyl acetate, 5/1 (v/v)). Tests for substrate scope were all performed with an analogous procedure.
58% With C21H29ClIrN4O2(1+)*CF3O3S(1-) In 1,2-dichloro-benzene at 150℃; for 2h; Inert atmosphere; Typical procedure for the dehydration of 1-phenylethanol (1 mol% catalyst loading) General procedure: Complex 1-4 (0.002 mmol), anisole(internal standard, 22 μL, 0.2 mmol), 1-phenylethanol (24 μL,0.2 mmol) and 1,2-dichlorobenzene (2 mL) were placed in a closedvial under nitrogen and heated at 150 °C. An aliquot (0.1 mL) wastaken at fixed times, diluted with CDCl3 (0.5 mL), and analyzed by1H NMR spectroscopy.
With phosphorus pentachloride
With hydrogenchloride
With hydrogenchloride Behandeln mit Pyridin;
With pyridine; hydrogenchloride at 125℃; im geschlossenen Rohr;
durch Destillation;
With acetic anhydride; trichlorophosphate
108 % Turnov. for 72h;
85 %Chromat. With LiCl-acidic alumina at 80℃; for 0.05h; Microwave irradiation;
With phosphorous acid fuctionalized vinyl silica gel In toluene at 75℃; for 5h; Inert atmosphere; 28 Example 28 1-Phenyl-1-propanol (16.0 g, 0.12 mol), the compound (0.3 g) obtained in Example 9 and toluene (40 mL) were mixed andheated with stirring at 75 ° C for 5 hours under a nitrogen atmosphere. Diethyl ether (50 mL) was added and the mixture wasfiltered to remove the catalyst. The organic detergent was concentrated under reduced pressure at room temperature to giveβ-methylstyrene as a colorless oil with a conversion of 93%. The filtered catalyst and 1-phenyl-1-propanol (16.0 g) were addedto toluene (40 mL) and the same reaction was repeated to give β-methylstyrene as a colorless oil with a conversion of 92%.

  • 6
  • [ 673-32-5 ]
  • [ 637-50-3 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen In toluene at 20℃; for 18h; Autoclave;
94% With hydrogen In dichloromethane at 20℃; for 0.7h;
With hydrogen In ethanol; benzene at 30℃; for 6h; hydrogenation in presence of var. additives, (Li-salts);
With hydrogen In ethanol; benzene at 30℃; for 1.1h; Yield given;
99 % Chromat. With hydrogen In diethyl ether at 25℃;
With hydrogen In methanol; d(4)-methanol
With quinoline; hydrogen In diethyl ether
With Pd0005Pb0995; hydrogen In ethanol at 25℃;
With carbon monoxide; hydrogen In tetrahydrofuran at 70℃; for 6h; Autoclave; 2.3. General experimental procedure for synthesis of alkenes viasemi-hydrogenation of alkynes General procedure: To a 100 mL high-pressure reactor, phenylacetylene (1 mmol),Pd (0.96 mol%) in a 10 mL THF were transferred under an inertatmosphere. The reactor was flushed three times with nitrogen then pressurized with desired 150 psi of syngas, then heated at70C with constant stirring (400 rpm) for 6 h. After the comple-tion of reaction, the reactor cooled down to room temperature andthe remaining syngas was carefully depressurized. The resultantreaction mixture filtered off by simple filtration. The filtrate was then collected in sample vial and the product was extracted for fur-ther analysis such as GC, GC-MS,1H &13C NMR and matched with those of authentic data. Selective experiments were performed in triplicate and it was observed that results showed variation of ±2%.
With hydrogen In hexane at 25℃; Autoclave; Liquid-Phase Hydrogenation General procedure: The liquid-phase hydrogenation of phenylacetylene(98%, Aldrich) and other substrates (styrene,diphenylacetylene, 1-phenyl-1- propyne, 1-phenyl-1-butyne, and 4-octyne; all of the substrates with 99%purity were purchased from Aldrich) were carried out inan autoclave type reactor with a magnetic stirrer and agas supply system. The autoclave was equipped with asampling system and an electronic pressure gage for themonitoring of the degree of hydrogen absorption. Thereaction was performed in n-hexane (98%, Merck) at25°C and an initial hydrogen pressure of 10 bar. Thecatalyst sample weight and the intensity of stirring werechosen to perform the process in the kinetic region. Theprocedure used for the determination of process conditionswas described in detail earlier [27].
With hydrogen In ethanol at 50℃; for 5h;
With hydrogen In hexane at 25℃; Autoclave; Liquid-Phase Hydrogenation of Substituted Alkynes General procedure: In this work the following reagent were used:diphenylacetylene, 1-phenyl-1-propyne, 1-phenyl-1-butyne, and phenylacetylene (all had 99% purity,Sigma-Aldrich); n-hexane (98%, Merck); gases andgas mixtures (Linde Gas, Balashikha, Russia).The reaction of liquid-phase hydrogenation wascarried out in an autoclave-type reactor at a temperatureof 25°C and an initial hydrogen pressure of 5 barwith uninterrupted stirring. A catalyst sample, 6 mL ofthe solvent (n-hexane), and 170 mg of alkyne substratewere placed in the reactor, after which the reactor wasloaded into an autoclave and connected to a gas dosingunit and an electronic pressure sensor to monitor thedegree of hydrogen absorption. To correctly comparethe catalytic characteristics of the studied samples, the reaction was carried out in the kinetic mode. To checkif the reaction is controlled by kinetics, the dependenceof the reaction rate and TOF on the degree ofgrinding the catalyst particles, the weight of the catalystand the stirring intensity of mixing of the reactionmixture was studied [33]. Before carrying out the reaction,a flow of high purity argon (~30 mL/min, 3 h)passed through the solvent to remove impurities of dissolvedoxygen. The selectivity to an olefin (S=) wasdetermined according to gas chromatographic analysisof the reaction mixture on a Crystal 5000 chromatograph(Khromatek, Russia) with a flame ionizationdetector. The calculation method is given in [34].Given that the hydrogenation of the alkyne substrateoccurs consecutively (first to the correspondingalkene then to alkane) the amount of the completehydrogenation product formed in the first stage ofhydrogenation is insignificant. The hydrogenation ofthe residual alkyne to alkane in the second stage of thereaction can also be neglected. Taking into accountthese assumptions, the reaction rate r ( gcat min-1)for each stage of hydrogenation was determined fromthe plot of the amount of absorbed hydrogen versustime of the process [34]. The kinetic selectivity of thereaction was estimated from the ratio of the rates ofalkyne hydrogenation in the first and second stages(r1/r2). The specific activity (TOF) of the samples wascalculated as the ratio of the number of molecules ofthe converted substrate to the total number of palladiumatoms in the catalyst per minute [35].
With platinum doped titanium oxide In methanol at 20℃; for 6h; Inert atmosphere; Irradiation;
With hydrogen
With hydrogen In cyclohexane at 79.84℃; for 1.5h; Autoclave;

Reference: [1]Mitsudome, Takato; Yamamoto, Masaaki; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Journal of the American Chemical Society, 2015, vol. 137, # 42, p. 13452 - 13455]
[2]Murata, Makoto; Tanaka, Yuko; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi [Chemistry Letters, 2005, vol. 34, # 2, p. 272 - 273]
[3]Urabe, Kazuo; Tanaka, Yoshiyuki; Izumi, Yusuke [Chemistry Letters, 1985, p. 1595 - 1596]
[4]Urabe, Kazuo; Tanaka, Yoshiyuki; Izumi, Yusuke [Chemistry Letters, 1985, p. 1595 - 1596]
[5]Fowley, Lissa A.; Michos, Demetrius; Luo, Xiao-Liang; Crabtree, Robert H. [Tetrahedron Letters, 1993, vol. 34, # 19, p. 3075 - 3078]
[6]Aguilar, Juan A.; Elliott, Paul I. P.; Lopez-Serrano, Joaquin; Adams, Ralph W.; Duckett, Simon B. [Chemical Communications, 2007, # 11, p. 1183 - 1185]
[7]Zhao, Yu; Mitra, Aurpon W.; Hoveyda, Amir H.; Snapper, Marc L. [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8471 - 8474]
[8]Niu, Wenxin; Gao, Yongjun; Zhang, Weiqing; Yan, Ning; Lu, Xianmao [Angewandte Chemie - International Edition, 2015, vol. 54, # 28, p. 8271 - 8274][Angew. Chem., 2015, vol. 127, p. 8389 - 8392,4]
[9]Jagtap, Samadhan A.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Journal of Molecular Catalysis A: Chemical, 2016, vol. 414, p. 78 - 86]
[10]Mashkovsky; Markov; Bragina; Rassolov; Baeva; Stakheev, A. Yu. [Kinetics and Catalysis, 2017, vol. 58, # 4, p. 480 - 491][Kinet. Katal., 2017, vol. 58, # 4, p. 508 - 520,13]
[11]Zhang, Junbo; Xu, Weiwei; Xu, Lai; Shao, Qi; Huang, Xiaoqing [Chemistry of Materials, 2018, vol. 30, # 18, p. 6338 - 6345]
[12]Rassolov; Bragina; Baeva; Smirnova; Kazakov; Mashkovsky; Stakheev, A. Yu. [Kinetics and Catalysis, 2019, vol. 60, # 5, p. 642 - 649][Kinet. Katal., 2019, vol. 60, # 5, p. 644 - 651,8]
[13]Lian, Juhong; Chai, Yuchao; Qi, Yu; Guo, Xiangyang; Guan, Naijia; Li, Landong; Zhang, Fuxiang [Chinese Journal of Catalysis, 2020, vol. 41, # 4, p. 598 - 603]
[14]Huang, Lingqi; Hu, Kecheng; Ye, Ganggang; Ye, Zhibin [Molecular catalysis, 2021, vol. 506]
[15]Gao, Ruijie; Lim, Jongwoo; Pan, Lun; Peng, Chong; Wang, Jian; Xu, Jisheng; Yang, Huaming; Zhang, Xiangwen; Zou, Ji-Jun [Journal of the American Chemical Society, 2022, vol. 144, # 1, p. 573 - 581]
  • 7
  • [ 700-06-1 ]
  • [ 637-50-3 ]
  • 2-methyl-3-phenyl-1,2,3,4-tetrahydrocyclopenta<b>indole [ No CAS ]
  • 8
  • [ 637-50-3 ]
  • [ 698-87-3 ]
  • [ 93-54-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; diphenylamine borane; dihydrogen peroxide 1.) THF, 0 deg C, 1 h; 20 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: 1-phenylpropene With C6H14BN; iodine In dichloromethane at 20℃; Stage #2: With sodium hydroxide; dihydrogen peroxide In methanol; water
  • 9
  • [ 637-50-3 ]
  • [ 2157-50-8 ]
YieldReaction ConditionsOperation in experiment
40% With sodium tetrahydroborate; tert.-butylnitrite; iron(II) phthalocyanine; hydrogen In ethanol at 20℃; for 3h;
8% With ethyl nitrite; tetraethylammonium borohydride In benzene for 72h; Ambient temperature;
  • 10
  • [ 637-50-3 ]
  • [ 4436-22-0 ]
YieldReaction ConditionsOperation in experiment
100% With 2,2,2-trichloroethylperoxycarbonic acid In dichloromethane for 5h; Ambient temperature;
98% With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; <i>tert</i>-butyl alcohol at 20℃; for 1h; Green chemistry;
98% With 3,3-dimethyldioxirane In acetone at 20℃; for 1h;
95% With sodium peroxoborate tetrahydrate; Biliton; acetonitrile In water at 20℃; for 18h;
94% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique; 3.1. General Procedure for the Synthesis of mesoepoxides1 General procedure: m-CPBA (approx. 70% pure material, 1.5 equiv) wasadded in portions to a stirred solution of the alkene 2 (1equiv) in CH2Cl2 (0.2 M) at room temperature under nitrogen.After 16h at room temperature, a saturated aqueousNa2S2O3 solution was added and the white solid was filteredon a celite pad and washed with CH2Cl2. The two phaseswere separated. The organic layer was washed with a saturatedaq. NaHCO3 solution and brine, and then dried overNa2SO4. After filtration and evaporation of the solvent underreduced pressure, the crude material was recovered in 34%-99% yields. All epoxides 1 resulted to be enough pure andwere used for the next reactions without further purifications.
93% With potassium caroate In aq. phosphate buffer; acetonitrile at 20 - 25℃; for 4h;
91% With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane; potassium hydroxide In acetonitrile at 20℃; for 1.83333h; Epoxidation of alkenes (Scheme 2, entry 2) General procedure General procedure: To a stirred solution of alkene (1 mmol) and THPDPE (1.5 mmol) in CH3CN (4 mL), KOH (1 M, 1 mL) was added and the mixture was stirred at room temperature for an appropriate time. After the completion of the reaction as monitored by TLC (hexane- Ethyl Acetate, 8:2) the mixture was quenched with Na2SO3 solution (3 M, 1 mL) and extracted with CH2Cl2 (3 × 5 mL). All of the products were characterized on the basis of their melting points, IR, 1H NMR, and 13C NMR spectral analysis and compared with those reported
90% With 1-decanoic acid; C28H38F6FeN4O8S2; dihydrogen peroxide In acetonitrile at 0℃; for 0.5h; enantioselective reaction;
90% With tert.-butylhydroperoxide In water; acetonitrile at 82℃; for 12h; Sealed tube; 5. Representative procedure for the epoxidation of alkenes General procedure: The CoNPs/MgO catalyst was activated by heating in an oven at 150 °C for 1 h. To avigorously stirred suspension of the CoNPs/MgO catalyst (10 mg) in MeCN (1.0mL) under air the corresponding alkene (0.5 mmol in 1.0 mL MeCN) and TBHP (63 μL of an 80 wt % solution in H2O, 0.5 mmol in 1.0 mL MeCN) were added and thesealed reaction flask was immersed in an oil bath at the reflux temperature ofMeCN (82 °C). The reaction mixture was stirred at this temperature until nofurther conversion of the starting alkene was observed (TLC, GC). Then, the reactionmixture was centrifuged and the supernatant removed. The solvent was evaporated invacuo, and the crude product was purified by flash column chromatography (silicagel, hexane/AcOEt) to give the corresponding epoxide. The recovered solid catalystwas washed with acetonitrile (3 × 2 mL) and dried in oven (150 °C, 1 h) for its reuse.
89% With [bis(acetoxy)iodo]benzene; C45H30F15FeN4O2*C8H8O2 In water; acetonitrile at 50℃; for 0.166667h; General procedure for catalytic oxidations General procedure: Unless otherwise indicated, all catalytic reactions were typicallycarried out in the presence of a small amount of H2O (5 L) with1 mol of catalyst (ca. 0.5 mol%), 0.2 mmol of organic substrate and1.2 equivalent of PhI(OAc)2(0.24 mmol) in 0.5 mL of acetonitrile at23C or 50C in a water bath. Aliquots of the reaction solution atconstant time interval were analyzed by GC/MS to determine theconversions, formed products and yields with an internal standard.The pure products were isolated by a flash column chromatography(silica gel with CH2Cl2and hexane mixture) to give isolated yields(Table 1, entry 3 and Table 2, entries 1-9). All reactions were run2 to 3 times, and the data reported represent the average of these reactions.
89% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; Inert atmosphere;
88% With ISOPROPYLAMIDE; Mg10Al2(OH)24CO3; dihydrogen peroxide; sodium dodecyl-sulfate In 1,2-dichloro-ethane at 70℃; for 18h;
87.6% With C30H25ClCoN3OP; dihydrogen peroxide; 1-ethyl-3-methylimidazolium hexafluorophosphate In water at 20℃; for 1h; Green chemistry; General procedure for the catalytic reaction General procedure: In a typical reaction, the catalyst (8mg, 2.4mmol) was dissolved in [Emim]PF6 (1 cm3). After addition of the substrate (1mmol), hydrogen peroxide (30% in water) (2 mmol) was added. The reaction mixture was stirred at room temperature for about 1h. The completion of the reaction was monitored by GC-MS until the reactants have disappeared. After completion of the reaction, the reaction mixture was extracted with diethyl ether (3×3 cm3). The ether layer was collected and then a definite amount of toluene was added as an internal standard for GC analysis. The ionic liquid phase including the catalyst was washed with diethyl ether and dried prior to recycling. The epoxidation of the other olefins was carried out similarly with a little variation in reaction time (Table 2).
87% With Tetrahydrothiopyran-4-one; Oxone; edetate disodium; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 7.5h;
82% With 4-tert-butylperoxybenzoic acid In ethyl acetate; acetonitrile at 20℃; for 12h; Green chemistry; General procedure of the epoxides General procedure: A solution of 4-tert-butyltoluene (89.0 mg, 0.60 mmol), AQN-2-CO2H (1a, 0.3 mmol), AcOEt (2.5 mL), and MeCN (2.5 mL) in a pyrex tube (15 mm × 150 mm) equipped with O2-balloon was stirred and irradiated using the fluorescent lamp for 20 h. Then, an alkene was added to the reaction mixture at room temperature for period of time. The resulting solution was concentrated under reduced pressure and purified by PTLC gave the corresponding epoxide.
71% With 1H-imidazole; tert.-butylhydroperoxide; bis(acetylacetonato)dioxidomolybdenum(VI) In tetrachloromethane; benzene at 70℃; for 1h;
59% With iodosylbenzene; Cr(N,N'-ethylenebis(salicylideneaminato)(H2O)2)PF6 In pyridine; dichloromethane Ambient temperature;
51% With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 3h; Ambient temperature;
42% With Oxone; ammonium bicarbonate In water; acetonitrile at 20℃; for 2h;
23% With Isopropylbenzene at 105℃; for 24h; 27 Example 27: Preparation of 2-methyl-3-phenylethylene oxide Β-methylstyrene (124.4 mg, 1.0 mmol) was added to a 50 mL reaction tube, and 3 mL of cumene was added; then, the reaction was performed at 105 ° C. in an air atmosphere. After 24 hours, the reaction was complete. Then CH3NO2 was added as an internal standard for NMR analysis. The yield was 23%.
16% With [Fe(di(o-imidazol-2-ylidenepyridine)methane)(MeCN)2](PF6)2; dihydrogen peroxide In water; acetonitrile at 25℃; for 0.0833333h;
With pyridine; oxygen; Benzoylformic acid In benzene at 20℃; for 1h; Irradiation;
76.5 % Chromat. With sodium nitrate; dihydrogen peroxide In chloroform; water at 30℃; for 24h;
With oxygen; benzil In benzene at 0 - 4℃; for 0.666667h; Irradiation; var. temp., var. solv., with and without Dabco;
With Ru(VI)(octaethylporphyrin)(O)2 In methanol; dichloromethane
77 % Chromat. With chromyl nitrate In tetrachloromethane; dichloromethane at -78℃; for 1h; effects of dimethylforamide and tetramethylurea on epoxidation yields;
With 3,3-dimethyldioxirane In acetone at 20℃; for 6h;
Stage #1: 1-phenylpropene With manganese(II) acetate In methanol; acetone at 0℃; for 0.25h; Stage #2: With oxalic buffer; dihydrogen peroxide In methanol; acetone at 0 - 2℃; for 4.5h; Further stages.;
92 % Chromat. With [bis(acetoxy)iodo]benzene In dichloromethane at 40℃; for 48h;
15 %Spectr. With pyridine; Oxone; water-d2; sodium hydrogencarbonate In [D3]acetonitrile at 20℃; for 4h;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 3h;
94 %Chromat. With iron(III) chloride hexahydrate; dihydrogen peroxide; 1-(2,6-diisopropylphenyl)-1H-imidazole In tert-Amyl alcohol; water at 20℃; for 1h;
With isobutyraldehyde In acetonitrile at 35℃; for 8h;
> 99 %Chromat. With peracetic acid; disodium hydrogenphosphate; C52H40Mn2N8O4 In acetonitrile at 20℃; for 0.00416667h;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;
81 %Chromat. With (R,R)-[N,N'-dimethyl-N,N’-bis[((2-pyridinyl)-3,5-di(tert-butyl)benzyl)cyclohexane-1,2-diamine]MnII(OTf)2]; dihydrogen peroxide In water; acetonitrile at -20℃; for 2h; Inert atmosphere; Schlenk technique; enantioselective reaction;
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In water; acetonitrile; <i>tert</i>-butyl alcohol at 20℃; for 18h; Green chemistry;
With 3-chloro-benzenecarboperoxoic acid
With oxygen In 1,4-dioxane at 60℃; for 4h; Irradiation; Sealed tube;
With cytochrome P450 [T121A-N201K-N209S-Y385H-E418G-A103L-M118L-R120H-V123I-I326V-V327M-H385V-M391L] variant; oxygen; nicotinamide adenine dinucleotide phosphate; isopropyl alcohol; alcohol dehydrogenase at 20℃; for 2h; Enzymatic reaction;
With peracetic acid; 2C4H13B10O2(1-)*Mn(2+)*2H2O In dichloromethane at 0 - 20℃;
With 5Ni(2+)*2C48H26N4O8(4-)*4H2O*O(2-) In acetonitrile at 100℃; for 4h;
With [bis(acetoxy)iodo]benzene; trans-[RuII(2-(3-pyrazolyl)pyridine)(terpyridine)(OH2)](PF6)2 In dichloromethane at 20℃; for 24h; Inert atmosphere;
32 %Spectr. With (S)-N-((R)-3,3-dimethylbutan-2-yl)-3,3-dimethyl-2-(((1-methyl-1H-imidazol-2-yl)methyl)amino)butanamide; iron(III) chloride hexahydrate; dihydrogen peroxide In tert-Amyl alcohol; water at 20℃; for 1h; 3.2.1. Catalysis without Additive General procedure: To a solution of FeCl3 6 H2O (6.8 mg, 25.0 μmol, 5 mol%) in 9 mL 2-Me-2-BuOH, an imidazole basedligand (50.0 μmol, 10 mol%) was added at room temperature under air. After addition of the olefin (500μmol), H2O2 (30 wt% in H2O, 170 μL, 1.50 mmol) mixed with 830 μL 2-Me-2-BuOH was added via syringepump over a 1 h period. The reaction was quenched with 50 μL saturated aqueous Na2SO3 solution. Afterextraction with CH2Cl2, the organic phases were combined and evaporated to dryness. The crude mixture was filtered through a SiO2-plug (1 cm, eluted with CH2Cl2). In order to determine the yield via 1H-NMR,pyrazine was added in a defined amount as an internal standard. Afterwards, purification was carriedout by means a preparative TLC plate (hexane/ethyl acetate) for the HPLC sample preparation in orderto determine enantioselectivity.
With K16H15Li7[Pr2(H2O)3(pyrazine-2,3-dicarboxylato)As3W29O103]2*38H2O; dihydrogen peroxide In water; butan-1-ol at 65℃; for 12h;
With dihydrogen peroxide In water at 20℃; for 7h;
88 %Chromat. With oxygen; Ti82-O)8[Cu(μ2-O)22-OH)]2(1,4-benzenedicarboxylato)6Li2; isobutyraldehyde In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Inert atmosphere;
With 3-chloro-benzenecarboperoxoic acid

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  • 11
  • [ 637-50-3 ]
  • [ 23355-97-7 ]
  • [ 4541-87-1 ]
YieldReaction ConditionsOperation in experiment
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 4h; Ambient temperature; Yield given. Yields of byproduct given;
With Oxone; sodium hydrogencarbonate at 23℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With dihydrogen peroxide; sodium hydroxide In methanol at 25 - 80℃; for 24h; Overall yield = 83 percent; Optical yield = 60 percent de; diastereoselective reaction; 4 Example 4: Comparison of diastereoselective epoxidation of / Z mixed olefins and E-olefins Reaction operation: At 25 , add olefin (1mmol), methanol (3mL), hydrogen peroxide (H2O2) (30%, 0.3mL), aqueous sodium hydroxide (NaOH) (5mol / mL) After stirring at room temperature for 3 hours, the product was isolated by column chromatography.Reaction 1 uses β-methylstyrene mixed with E / Z as raw material, and the diastereomer selectivity of the epoxidation product is 1: 4; Reaction 2 uses E-β-methylstyrene as raw material, epoxidation The diastereomer selectivity of the product is greater than 99: 1, product 28: (trans) -2-methyl-3-phenyloxirane
  • 12
  • [ 22293-10-3 ]
  • [ 637-50-3 ]
  • [ 98-85-1 ]
  • [ 36065-27-7 ]
  • [ 729-43-1 ]
  • 13
  • [ 4436-22-0 ]
  • [ 637-50-3 ]
YieldReaction ConditionsOperation in experiment
94% With carbon monoxide In tetrahydrofuran; water at 110℃; for 3h; Autoclave; chemoselective reaction;
70% With sodium tetrahydroborate In ethanol; acetonitrile at 25℃; for 3h;
98 %Chromat. With isopropyl alcohol In toluene at 110℃; for 4h; Inert atmosphere; chemoselective reaction;
  • 14
  • [ 637-50-3 ]
  • [ 201230-82-2 ]
  • [ 5445-77-2 ]
  • [ 2439-43-2 ]
YieldReaction ConditionsOperation in experiment
1: 92.8% 2: 7.2% With hydrogen In benzene at 90℃; for 48h;
With acetylacetonatodicarbonylrhodium(l); trisodium tris(3-sulfophenyl)phosphine; heptakis(2,6-di-O-methyl)cyclomaltoheptaose; hydrogen In water at 80℃; for 6h; stainless steel autoclave; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 15
  • [ 637-50-3 ]
  • [ 15497-51-5 ]
  • trans-1,3-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline [ No CAS ]
  • cis-1,3-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tin(IV) chloride In dichloromethane at 0℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 16
  • [ 637-50-3 ]
  • [ 104-55-2 ]
YieldReaction ConditionsOperation in experiment
92% With tert.-butylhydroperoxide; Ru(2,4,13,15-tetraphenyl-1,5,12,16-tetraaza-tricyclo[14.2.2.06,11]eicosa-4,6(11),7,9,12-pentaene)Cl2 In acetonitrile at 20℃; for 3h; Irradiation; 2.4.1 C-H bond activation of methylstyrenes General procedure: To a solution of Zn(II)/Ru(II) complex (1.25μmol), methylstyrenes (0.5mmol) and TBHP (1.0mmol) in 10mL of acetonitrile was added at room temperature. After the reaction was stirred under visible light for three hours, (monitored the reaction by LC-MS) solvent was distilled under reduced pressure. Purification of crude products by column chromatography with hexane/dichloromethane (9:1, v/v) as eluent to an afforded pure product (Scheme 2).
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water Ambient temperature; Yield given;
With dichloro bis(acetonitrile) palladium(II); 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 16h;
  • 17
  • [ 623-73-4 ]
  • [ 637-50-3 ]
  • [ 97023-66-0 ]
YieldReaction ConditionsOperation in experiment
89% at 80℃; for 4h;
79% With sodium tetrachloroaurate dihydrate; 1-octyl-3-methylimidazolium hexafluorophosphate at 20℃; for 26h;
60% With aqua-bromo-dicarbonyl-[1-benzyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene]ruthenium(II) trifluoromethylsulfonate In dichloromethane at 20℃; for 6h; Inert atmosphere;
27% With Au-TiO2 In toluene at 70℃; for 24h; Sealed tube;
With 1-methyl-1H-imidazole; C52H36CoF34N2O2 In benzene at 20℃; Inert atmosphere;
With 2-amino-2-hydroxymethyl-1,3-propanediol In acetonitrile
75 %Chromat. With [Cu(NH2C2H4NH2)3][B(C6F5)4]2 In dimethyl sulfoxide at 24.84℃; for 24h; 2.4. Cyclopropanation General procedure: (0.114 g, 1.0 mmol) Ethyl diazoacetate (EDA) in 2.0 ml of DMSO was slowly added (addition time 1hr.) to a 4.0 ml DMSO solution of an (5 mmol) olefin and (0.02 mmol) of prepared complexes (1-6 ). The reaction was followed and products were identified by GC-MS.

  • 18
  • [ 637-50-3 ]
  • aqueous ammonium polysulfide [ No CAS ]
  • [ 102-93-2 ]
  • 19
  • [ 637-50-3 ]
  • [ 100-52-7 ]
YieldReaction ConditionsOperation in experiment
83% With aluminum oxide; potassium permanganate In dichloromethane at 20℃;
83% With sodium paraperiodate; sulfuric acid In water at 70℃; for 3.5h;
73% With oxygen In water; acetonitrile at 36℃; for 10h; Irradiation;
65% With cobalt(II) 5,10,15,20-tetraphenylporphyrin; naphthalene; oxygen; isovaleraldehyde at 80℃; for 4h;
52 %Chromat. With potassium permanganate; copper(ll) sulfate pentahydrate for 0.133333h; Neat (no solvent); Microwave irradiation;
With [bis(acetoxy)iodo]benzene; [(2,2':6',2'-terpyridine)(Cl)RuII(9-oxidophenalenone)] In dichloromethane at 24.84℃; for 16h; 2.6 General methods for catalytic reaction General procedure: In a typical reaction, the catalyst (0.01 mmol) and 2 equivalent of PhI(OAc)2 in 3 mL of dichloromethane were placed in a 25 mL Schlenk tube and the mixture was stirred for 10 min. The solution immediately turned to reddish brown. The corresponding alkenes and dodecane (1.5 mmol each) were then added in additional 1 mL of solvent and then stirred at room temperature for 16 h at 298 K (353 K for aliphatic substrates). Then the reaction mixture was filtered through a short silica gel column using dichloromethane as eluent prior to GC analysis. The percent conversion and percent selectivity were determined either by GC against authenticated sample with respect to dodecane as an internal standard or by 1H NMR.
With sodium periodate; C24H28ClN4O2Ru(1+)*F6P(1-) In dichloromethane; water; acetonitrile at 25℃; for 0.0833333h; Inert atmosphere;
62 %Spectr. With tetrafluoroboric acid; iodobenzene; 1,1,1,3',3',3'-hexafluoro-propanol; 3-chloro-benzenecarboperoxoic acid In water; toluene at 35℃; 4.1 General procedure for the syntheses of 2 General procedure: To a 10 mL sealed tube styrenes (0.2 mmol) and m-CPBA (89.15 mg, 2.2 equiv.) were added. Then PhI (5 μL, 20 mol%), HBF4 (28 μL, 2.2 equiv.), toluene (1.2 mL) and H2O (0.4 mL) were added. The vessel was sealed with a teflon-lined cap, and the mixture was stirred at 35 oC. After reaction was completed, the saturated NaHCO3 solution was added. 1,1,2,2-Tetrachloroethane was added as an internal standard to calculate the NMR yield.
15 %Chromat. With titanium(IV) oxide; dihydrogen peroxide In water; acetonitrile at 50℃; for 16h; Typical procedures for H2O2 thermal oxidation General procedure: The oxidation of styrenes was performed in a 15 mL test tube. 0.10 g (1 mmol) styrene was stirred with 100 mg TiO2 in 1.0 mL acetonitrile. Subsequently, 1.0 ml H2O2 (15 wt%) was added into the mixture. The resulting mixture was stirred at 50 °C for 16 h. After reaction, the solution was cooled to room temperature, then diluted with 12 mL ofacetonitrile and filtered. Biphenyl (40 mg, 0.25 mmol) was added to the solution as an internal standard for gas chromatography (GC) analysis. The solution was placed under ultrasonic irradiation for 10 min to ensure a good homogeneity of the mixture. The conversion and yield were determined on the basis of the analysis of the mixture by GC.

  • 20
  • [ 637-50-3 ]
  • [ 1855-09-0 ]
YieldReaction ConditionsOperation in experiment
94% With oxygen; 4-methylmorpholine N-oxide In water; acetone at 25℃; for 2h;
81% With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 3h;
45% With seleno-L-cystine; water; dihydrogen peroxide at 20℃; for 168h; Optical yield = 32 %de; stereoselective reaction; 2 4.2 General procedure for dihydroxylation of olefins General procedure: 0.006 mmol of l-selenocystine (3) and 2.39 mmol of H2O2 30 wt % were stirred in water (1 mL) at room temperature for 10 min and 0.6 mmol of substrate were subsequently added. The reaction was monitored by TLC and by GCMS and after the time reported in Table 2 the aqueous mixture was extracted (three times) with EtOAc. The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by flash chromatography on a silica gel column using a mixture of MeOH/EtOAc (2:98) as eluant. The structures of the products and the relative yields are reported in Table 2.
With Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; <i>tert</i>-butyl alcohol at 20℃; for 1.5h;
With dihydrogen peroxide; nitric acid; potassium iodide In water; acetonitrile at 24.84℃; for 4h;

  • 21
  • [ 637-50-3 ]
  • [ 88196-06-9 ]
YieldReaction ConditionsOperation in experiment
98% With 4-methylmorpholine N-oxide In water; acetone at 100℃; for 3h; General procedure for the dihydroxylation of alkenes General procedure: alkenesTo a stirred solution of alkene (1, 1 mmol) in a mixture ofacetone:H2O 2:1 (3 mL) in a pressure tube, OsO2-Fe3O4(10 mg,0.08% of osmium) and NMO (234 mg, 2 mmol) were added. Theresulting mixture was stirred at 100C during 3 h. The catalyst wasremoved by a magnet and the resulting solution was extracted withether. The organic phases were dried over MgSO4, and the solventswere removed under reduced pressure. The product was usuallypurified by chromatography on silica gel (hexane/ethyl acetate)to give the corresponding products 2 or 4. Physical and spectro-scopic data as well as literature for all compounds are includedas Appendices A and B. FT-IR spectra were obtained on a Nicoletimpact 400D spectrophotometer. NMR spectra were recorded ona Bruker AC-300 apparatus (300 MHz for1H and 75 MHz for13C)using CDCl3as a solvent and TMS as internal standard for1H and13C; chemical shifts are given in (parts per million) and couplingconstants (J) in Hertz. Mass spectra (EI) were obtained at 70 eVon a spectrometer Agilent GC/MS-5973N, giving fragment ions inm/z with relative intensities (%) in parentheses. Thin layer chro-matography (TLC) was carried out on DC-Fertigfolien ALUGRAMplates coated with a 0.2 mm layer of silica gel; detection by UV254light, staining with phosphomolybdic acid [25 g phosphomolybdicacid, 10 g Ce(SO4)2·4H2O, 60 mL of concentrated H2SO4and 940 mLH2O]. Column chromatography was performed using silica gel 60of 35-70 mesh.
92% With CF3O3S(1-)*C20H18F6N4O6OsS2(1+); dihydrogen peroxide In water; <i>tert</i>-butyl alcohol at 70℃; for 4h; Inert atmosphere; diastereoselective reaction;
85% With 4-methylmorpholine N-oxide In water; acetone at 20℃; for 3.5h; Inert atmosphere; For Table 3, Entries 1-10 General procedure: A mixture of alkene (250 mol), 5% Os/CR11 (9.5 mg, 2.50 mol, 1 mol%), NMO (32.2 mg, 275mol), and acetone-H2O (7 : 3, 0.5 mL) in a 15 mL-test tube was stirred under an Ar atmosphere atroom temperature. After the specific time [the consumption of the starting material was confirmedby TLC analysis (hexane-EtOAc)], the mixture was filtered through a Celite pad, and the pad waswashed with acetone (30 mL) and concentrated in vacuo. The residue was purified by columnchromatography on silica gel (hexane-EtOAc) to give the corresponding diol
82% With dihydrogen peroxide; triethylammonium acetate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water; acetone at 20℃; for 16h;
With Quinuclidine; osmium(VIII) oxide; <i>tert</i>-butyl alcohol In acetone at 25℃; for 12h;
83 %Spectr. With [OsIII(OH)(H2O)(N,N’-dimethyl-2,11-diaza-[3.3](2,6)pyridinophane)](PF6)2; dihydrogen peroxide In water; butan-1-ol at 70℃; for 5h; Inert atmosphere; Green chemistry;
Multi-step reaction with 2 steps 1: 2,2,2-Trifluoroacetophenone; dihydrogen peroxide / <i>tert</i>-butyl alcohol; acetonitrile; water / 18 h / 20 °C / pH 11 / Green chemistry 2: (1S)-10-camphorsulfonic acid / <i>tert</i>-butyl alcohol; acetonitrile; water / 2 h / 20 °C

  • 22
  • [ 637-50-3 ]
  • [ 870-50-8 ]
  • N-(1-phenylpropyl)-N'-(tert-butoxycarbonyl)hydrazinecarboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With phenylsilane In isopropyl alcohol at 0℃; for 2h;
  • 23
  • [ 637-50-3 ]
  • [ 14212-53-4 ]
  • (1R,2S)-1,2-Epoxy-1-phenylpropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4,5]decane-8,9-diyl diacetate; potassium peroxomonosulfate; ethylenediaminetetraacetic acid; tetrabutylammonium hydrogensulfate; potassium carbonate In Dimethoxymethane; lithium hydroxide monohydrate; acetonitrile at 0℃; for 8h; aq. phosphate buffer; optical yield given as %ee;
71 % ee With C23H35F3MnN4O4S(1+)*CF3O3S(1-); dihydrogen peroxide; glacial acetic acid In lithium hydroxide monohydrate; acetonitrile at 0℃; for 1h; Inert atmosphere; enantioselective reaction;
82 % ee With C68H66N4O10Ti2; dihydrogen peroxide; sodium chloride In dichloromethane; lithium hydroxide monohydrate at 16.84℃; for 24h; enantioselective reaction; 2.2. Typical asymmetric epoxidation procedure General procedure: A conjugated olefin (0.10 mmol) was added to the Ti-salan orTi-salalen catalyst (5 mol or 0.8 mol, respectively) dissolved inCH2Cl2(0.4 mL), and 0.05 mL of a saturated aqueous NaCl wasadded. The mixture was thermostatted at the desired temperature(290 K), and 30% aqueous hydrogen peroxide (0.20 mmol of H2O2)was then introduced in one portion. Stirring (400 rpm) was contin-ued at that temperature for (typically) 24 h. The reaction mixturewas diluted with aqueous NaCl (1 mL), the organic phase was sepa-rated, and the aqueous phase was extracted with CH2Cl2(3 × 1 mL).The combined organic extract was dried with CaSO4, diluted with0.6 mL of CCl4, and CH2Cl2was carefully removed on a rotary evap-orator at room temperature. The remaining solution was dilutedwith 0.1 mL of CDCl3and analyzed by1H NMR to reveal the ratioof olefin, epoxide, and byproduct(s), and by chiral HPLC to measurethe ee of the epoxide.
79 % ee With sodium percarbonate; EBA; C30H44F6MnN6O6S2 In acetonitrile at -40℃; for 2h; Overall yield = 99 percent; enantioselective reaction; 3.3. General Procedure for the Catalytic Epoxidation of Olefins with Sodium Percarbonate In a typical experiment, substrate (100 mol) and carboxylic acid (1.4 mmol) wereadded to the solution of the manganese catalyst (0.2 mol) in CH3CN (0.4 mL), andthe mixture was thermostated at 40 C. Then, 200 mol of mortar-grounded sodiumpercarbonate was added to the reaction mixture in 3 roughly equal portions, with 30 minintervals between the additions (66.7 mol in each portion). The resulting mixture wasstirred for 2 h at 40 C (total reaction time: 3 h). The reaction was quenched witha saturated aqueous solution of Na2CO3, and the products were extracted with Et2O(3 4 mL). The solvent was evaporated, and the residue was analyzed by 1H NMRspectroscopy (Table S1, Figure S1, SI) to determine conversions and yields and by HPLC onchiral stationary phases (Table S2, Figure S2, SI) to measure the enantiomeric excess valuesof the chiral epoxides as previously described [12,30,32].

  • 25
  • [ 637-50-3 ]
  • [ 22436-06-2 ]
  • 26
  • [ 637-50-3 ]
  • (2S*,3R*)-2-methyl-3-phenyloxirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetraphenylphosphonium monoperoxysulfate In chloroform at -40 - 40℃; for 24.25 - 24.3333h; Cis-p-methylstyrene oxide: Tetraphenylphosphonium monoperoxysulfate (2 eq, 0.768 g, 1.70 mmol) was dissolved in chloroform (16 ml) and cooled to-40°C. To this was added the iminium salt, (+)- [ (4S, 5S) - 2, 2-dimethyl-4- [4- (methylsulfonyl)-phenyl]-1, 3-dioxan-5-yl]-3, 4-dihydroisoquinolinium tetraphenylborate, (10 mol %, 0.061 g, 0.09 mmol) as a solution in chloroform (4 ml). This iminium salt solution was cooled to the same temperature as the solution containing the oxidant and added dropwise over 15-20 min, the temperature of the reaction vessel was monitored to minimize increase in temperature during the addition. The substrate (0.10 g, 0.85 mmol) was also added as a solution in chloroform (4 ml) in the same manner as the catalyst. The reaction was stirred at-40°C for 24 h. Diethyl ether (20 ml) (pre-cooled to-40°C) was then added to precipitate the remaining oxidant. The solution was filtered through Celite. Solvents were removed under reduced pressure to afford a pale yellow oil. Column chromatography eluting with ethyl acetate/light petroleum 1: 99 gave the product as a colourless oil (0.97 g, 85% yield, 70% ee, (+)-1 S, 2R). vmaX (neat)/cm-' 3061,2994, 1604,1496, 1450,1258, 1149,9563, 853,742, 700,619 ; 6H (250 MHz; CDCI3) 1.12, (3H, d, J 5.4 Hz), 3.32-3. 40 (1H, m), 4.08 (1H, d, J 4.3 Hz), 7.24-7. 39 (5H, m); 8c (62.5 MHz; CDCI3) 12.84, 55.37, 57.78, 126.85, 127.74, 128.26, 135.84.
  • 27
  • K2CO3-AcOH [ No CAS ]
  • Oxone [ No CAS ]
  • [ 637-50-3 ]
  • (2S,3R)-2-methyl-3-phenyloxirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With K2CO3; Bu4NHSO4; triethylamine In aqueous EDTA; DME-DMM; pentane Representative Asymmetric Epoxidation Procedure Representative Asymmetric Epoxidation Procedure To a solution of cis-β-methyl styrene (0.059 g, 0.5 mmol) and ketone IVd (0.026 g, 0.075 mmol) in DME-DMM (3:1, v/v) (7.5 mL) were added buffer (0.2 M K2CO3-AcOH in 4*10-4 M aqueous EDTA, buffer pH=8.0) (5 mL) and Bu4NHSO4 (0.0075 g, 0.02 mmol) with stirring. After the mixture was cooled to about -10° C. (bath temperature) via a NaCl-ice bath, a solution of Oxone (0.212 M in 4*10-4 M aqueous EDTA, 4.2 mL) (0.548 g, 0.89 mmol) and K2CO3 (0.479 M in 4*10-4 M aqueous EDTA, 4.2 mL) (0.278 g, 2.01 mmol) were added dropwise separately over a period of 3.5 h via a syringe pump. The reaction was then quenched with the addition of pentane and extracted with pentane. The combined organic layers were washed with brine, dried (Na2SO4), filtered, concentrated, and purified by flash chromatography (the silica gel was buffered with 1% Et3N in pentane; pentane-ether (1/0 to 50/1 was used as eluent) to give cis-β-methylstyrene oxide as a colorless liquid (0.58 g, 87% yield, 91% ee).
  • 28
  • [ 1295-35-8 ]
  • [ 104-54-1 ]
  • [ 100-42-5 ]
  • [ 637-50-3 ]
  • [ 63576-88-5 ]
  • [ 7732-18-5 ]
  • [ 104-55-2 ]
  • 29
  • [ 637-50-3 ]
  • [ 698-87-3 ]
  • [ 93-54-9 ]
  • [ 931-16-8 ]
  • [ 38898-70-3 ]
  • 30
  • [ 637-50-3 ]
  • [ 2114-00-3 ]
YieldReaction ConditionsOperation in experiment
91% With dibromamine-T; sodium thiosulfate In water; acetone at 20℃; for 1h; General procedure: To a solution of olefin (1mmol) in acetone (3mL) and water (0.1mL), TsNBr2 (2.2mmol) was added at room temperature. After completion of reaction, sodium thiosulfate (200mg approx.) was added and the reaction mixture was stirred for another 10min. The reaction mixture was extracted with ethyl acetate, dried (Na2SO4) and concentrated. Purification of the crude product by flash chromatography on silica gel (230-400 mesh) with petroleum ether-EtOAc as eluent gave the pure product.
90% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water at 60℃; for 1h; Green chemistry;
83% With N-Bromosuccinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25 - 35℃; for 1.1h; regioselective reaction;
77% With dipotassium peroxodisulfate; potassium bromide In water at 60℃; for 12h; Green chemistry;
45% With hydrogen bromide; oxygen In water; ethyl acetate for 7h; Irradiation;
With N-Bromosuccinimide; water at 80℃; for 2h; Inert atmosphere; Green chemistry;
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water at 60℃; for 2h; 1 General procedure for the synthesis of aminothiazoles 2a-2ah General procedure: To a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of N-methylthiourea/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 °C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.

  • 31
  • [ 637-50-3 ]
  • [ 25015-63-8 ]
  • [ 916658-71-4 ]
YieldReaction ConditionsOperation in experiment
84% With [1,4-bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tris(pentafluorophenyl)borate In 1,1-Dichloroethylene at 70℃; for 9h;
84% With C39H48FeN2Si In benzene-d6 at 90℃; for 3h; Glovebox; Inert atmosphere; Schlenk technique;
38% With N-(2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl)picolinamide; sodium triethylborohydride; iron(II) chloride In tetrahydrofuran; toluene at 30℃; for 18h; Inert atmosphere; Schlenk technique; Green chemistry; regioselective reaction;
With B(C6F5)3; [Rh(C8H12)((C6H5)2P(CH2)4P(C6H5)2)]BF4*C4H8O In further solvent(s) (N2); treatment of styrene deriv. with pinacol borane in dichloroethane at 70°C in presence of rhodium compd. and perfluorophenylborane for 9 h; GC anal.;
In further solvent(s) (N2); treatment of styrene deriv. with pinacol borane in dichloroethane at 70°C in presence of rhodium compd. for 9 h; GC anal.;

  • 32
  • [ 637-50-3 ]
  • [ 10304-81-1 ]
YieldReaction ConditionsOperation in experiment
65% With 4-Methoxybenzenethiol; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; 2,6-lutidine hydrochloride In chloroform; 2,2,2-trifluoroethanol for 5h; Irradiation; Inert atmosphere; Methods General procedure: The general procedure for the anti-Markovnikov hydrochlorination of styrenesusing 2,6-lutidine hydrochloride (Method B) was as follows. In a typical experiment,a flame-dried 2 dram vial was equipped with a magnetic stir bar and 9-mesityl-10-methylacridinium tetrafluoroborate (1a, 30.8 mg, 0.0771 mmol, 5.0 mol%). The vialwas placed under an inert atmosphere and 2,6-lutidine hydrochloride (443 mg, 3.08mmol, 2.0 equiv.) was added. The solvent CHCl3/TFE (2.5:1 (vol:vol), 2.8 ml) wasadded to a concentration of ∼0.55 M. Liquid substrate (β-methylstyrene 3a, 200 μl,1.54 mmol, 1 equiv.) was added via microsyringe after the solvent. The hydrogenatom donor, 4-methoxythiophenol (2b, 37.9 μl, 0.308 mmol, 20 mol%), was addedvia microsyringe. The vial was sealed with a Teflon-coated septum cap, and thereaction mixture was irradiated (450 nm) for the time indicated. Upon completion,saturated aqueous sodium bicarbonate was added carefully and the two phases wereallowed to separate. The organic phase was collected, and the aqueous phase wasextracted with two portions of dichloromethane. The combined organic portionswere passed through a short plug of SiO2. The solvent was removed under reducedpressure. NMR yields were taken by integration against a known quantity ofhexamethyldisiloxane (HMDS) in CDCl3. The final products were isolated by silicagel chromatography using the conditions listed.
34% With chloroform at 250℃; for 7h; Inert atmosphere; Autoclave;
  • 33
  • [ 637-50-3 ]
  • [ 103980-88-7 ]
YieldReaction ConditionsOperation in experiment
93% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In toluene at 0℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
93% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In neat (no solvent) at 0℃; for 17h; Asymmetric hydrosilylation using P4 as a ligand under neat conditions: To polymer ligand P4 (13.3 mg, 2.0 μmol phosphorus atom) was added [PdCl(π-allyl)]2 (0.01 mM in toluene, 50 μL, 0.5 μmol). The solvent was evaporated in vacuo. Styrene (104.2 mg, 1.0 mmol) was added to the residual material, and the mixture was cooled to 0 °C. Trichlorosilane (0.15 mL, 1.5 mmol) was added at 0 °C, and the resultant solution was stirred at 0 °C for 17 h. After the reaction mixture was evaporated, the residual material was extracted with MeCN (1 mL × 3). The extracts were subjected to bulb-to-bulb distillation to afford the hydrosilylation product(222.8 mg, 93% yield).
92% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In toluene at 0℃; for 42h; Inert atmosphere; enantioselective reaction;
84% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In chloroform; 1,1,2,2-tetrachloroethane at 20℃; for 24h; Inert atmosphere; enantioselective reaction;

  • 34
  • [ 637-50-3 ]
  • [ 108438-43-3 ]
  • [ 1237776-21-4 ]
  • 35
  • [ 637-50-3 ]
  • [ 40421-52-1 ]
  • [ 90-63-1 ]
  • [ 4436-22-0 ]
  • 36
  • [ 64-17-5 ]
  • [ 108-88-3 ]
  • [ 637-50-3 ]
  • [ 620-14-4 ]
  • [ 611-14-3 ]
  • [ 103-65-1 ]
  • [ 622-96-8 ]
  • 37
  • [ 64-17-5 ]
  • [ 108-88-3 ]
  • [ 637-50-3 ]
  • [ 611-14-3 ]
  • [ 103-65-1 ]
  • [ 622-96-8 ]
  • 38
  • [ 637-50-3 ]
  • [ 98-86-2 ]
YieldReaction ConditionsOperation in experiment
81% With tert.-butylhydroperoxide; water at 90℃; for 12h;
37% Stage #1: 1-phenylpropene With N-iodo-succinimide; cetyltrimethylammonim bromide In 1,4-dioxane; water at 115℃; for 0.25h; Microwave irradiation; Stage #2: With dipyridinium dichromate; acetic acid In 1,4-dioxane; water at 115℃; for 0.25h; Microwave irradiation;
76 %Chromat. With oxygen; potassium carbonate In methanol at 130℃; for 12h; Sealed tube; Autoclave; 18 Example 18 Add Co-N-C (5 mol% relative to the substrate), 1-phenylpropene (1 mmol), K2CO3 (20 mol%), and 4 mL methanol into a 25 mL polytetrafluoroethylene-lined autoclave, Seal the reactor, fill it with oxygen pressure to 0.4MPa, put the reactor in an oil bath at 130°C, stir and react for 12h at 400 rpm, After the reaction, the reactor was cooled to room temperature, the reactor was opened, and the internal standard biphenyl (60mg) was added. The qualitative products were detected by gas chromatography-mass spectrometry, and the yields of the substrate 1-phenylpropene and the product 1-phenylacetaldehyde by the gas chromatography internal standard method are shown in Table 1.
  • 39
  • [ 637-50-3 ]
  • [ 64-19-7 ]
  • [ 4962-46-3 ]
YieldReaction ConditionsOperation in experiment
95% With dibromamine-T at 20℃; for 0.166667h; Inert atmosphere; General procedure for the bromoacetoxylation reaction General procedure: To a solution of olefin (1 mmol) in acetic acid (2 ml) TsNBr2 (1 mmol) were added under nitrogen atmosphere and stirred. After 10 minute of reaction, sodium thiosulfate (200 mg approx.) was added followed by the addition of water (5 mL). The reaction mixture was stirred for 15 minutes and taken up in ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography on silica gel (230-400 mesh) with petroleum ether/ethyl acetate (95:5) as eluent.
  • 41
  • [ 136918-14-4 ]
  • [ 637-50-3 ]
  • [ 3695-00-9 ]
  • N-(2-(1,3-dioxoisoindolin-2-yl)-1-phenylpropyl)-4-methyl-N-tosylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: phthalimide In dichloromethane at 70℃; for 1h; Stage #2: 1-phenylpropene; di(4-tosyl)amine With bis(tertbutylcarbonyloxy)iodobenzene In dichloromethane at 70℃; for 20h; Sealed vessel; 8 Example 8. Intermolecular palladium-catalysed diamination of terminal alkenes, with 10 mol% catalyst (Table 6, compounds (l)hh-kk).A Pyrex tube equipped with a stirrer bar is charged with 31 mg phatalimide (0.21 mmol, 1.0 eq), 8 mg bis(benzonitrile)palladiumdichloride (0.021 mmol, 10%) and 0.3 ml_ of absolute dichloroethane and the solution is stirred at 70°C for 1 h. Then, 81 mg bistosylamide (0.25 mmol, 1 .2 eq), 170 mg iodosobenzene dipivalate (0.42 mmol, 2.0 eq) and compounds(ll)hh/(ll)ii/(ll)jj/(ll)kk (0.21 mmol) were added, the resulting solution is sealed and stirred at 70°C for 20h. After that, the solution is transfered into a round botton flask and all volatile material is evaporated under reduced pressure. If not stated otherwise, the remaining solid is directly purified by column chromatography (silica gel, n-hexane/ethyl acetate, 3/1 , v/v) to give the corresponding product in analytically pure form. N-(-2-(1 ,3-dioxoisoindolin-2-yl)-1 -phenylpropyl)-4-methyl-N- tosylbenzenesulfonamide (l)hh1H NMR (400 MHz, CDCI3): 51 .01 (d, J = 6.9 Hz, 3H), 2.30 (s, 3H), 2.48 (s, 3H), 5.85 (dq, J = 1 1 .1 , 6.9 Hz, 1 H), 6.49 (d, J = 1 1 .1 hz, 1 H), 6.97 (d, J = 8.3 Hz, 2H), 7.02 (d, J = 8.6 Hz, 2H), 7.27-7.25 (m, 3H), 7.44 (d, J = 8.1 Hz, 2H), 7.63-7.60 (m, 2H), 7.71 (br, 2H), 7.78 (dd, J = 6.5, 3.0 Hz, 2H), 8.28 (d, J = 8.4 Hz, 2H). 13C NMR (400 MHz, CDCI3): δ = 15.7, 21 .6, 21 .9, 47.9, 63.6, 128.2, 128.6, 128.7, 128.9, 129.7, 129.9, 130.2, 134.1 , 135.1 , 136.5, 138.7, 144.1 , 145.5, 167.2, 168.7. IR (KBr): 3066, 2990, 1708, 1365, 1 165 cm"1. HRMS: calcd for C3iH28N206S2Na: 61 1 .1295, found: 61 1 .1287.
  • 42
  • [ 637-50-3 ]
  • [ 4486-44-6 ]
  • [ 1371552-18-9 ]
YieldReaction ConditionsOperation in experiment
69% With trifluoroacetic acid In dichloromethane at 20℃; for 24h; 1 A reaction vessel equipped with a magnetic stir-bar was charged with dichloromethane, Ga(III) triflate (5 mol%) , alkene (1 equiv) , phosphorothioic acid (1.2 equiv) , and the indicated amount of trifluoroacetic acid. The reaction was aged overnight at room temperature. The reaction was then quenched with saturated aqueous sodium bicarbonate, extracted three times with dichloromethane, washed with brine, dried over sodium sulfate and then concentrated under vacuum. The crude residue was purified using silica gel column chromatography to afford the desired hydrothiolated product .
  • 43
  • [ 637-50-3 ]
  • [ 21911-68-2 ]
  • [ 1391490-62-2 ]
YieldReaction ConditionsOperation in experiment
65% With iodine; oxygen In acetonitrile at 20℃; for 48h; Irradiation;
58% With indium(III) chloride; oxygen; tris(p-bromophenylammoniumyl) hexachloroantimonate In acetonitrile at 60℃;
37% With indium(III) chloride; tert.-butylnitrite; oxygen In acetonitrile at 60℃; for 13h;
  • 44
  • [ 637-50-3 ]
  • [ 145838-86-4 ]
  • (2S,3S)-dimethyl 2-methyl-3-phenylcyclopropane-1,1-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(actonitrile)copper(I) hexafluorophosphate; (4S,4's)-2,2'-(1,3-bis(4-(tert-butyl)phenyl)propane-2,2-diyl)bis(4-phenyl-4,5-dihydro-oxazole) In toluene at -40℃; for 103h; Molecular sieve; Inert atmosphere;
  • 45
  • [ 637-50-3 ]
  • [ 140-28-3 ]
  • [ 1421005-01-7 ]
YieldReaction ConditionsOperation in experiment
60% With HgO*2HBF4 In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; General procedure for the synthesis of piperazines General procedure: Olefins 1 (1 mmol) were dissolved in dry THF (15 mL) under N2 and HgO·2HBF4 (1.1 mmol) was added portionwise followed by the addition of N,N′-disubstitutedethylene diamine 2 (1.5 mmol). The reaction mixture was stirred at 70 °C for the appropriate time as shown in Table 1. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with water and extracted with CH2Cl2 (3 × 30 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo, and purified by flash column chromatography on silica gel to afford corresponding protected piperazine derivatives 3. The compound 3 was dissolved in MeOH (9 mL) containing acetic acid (1 mL) and then added Pd/C.27 The reaction mixture was stirred for 4 h under H2 on a Parr hydrogenator and the progress of the reaction was monitored on TLC. After completion of reaction, the catalyst was filtered off and the organic mixture was evaporated in a rota-vapour. The crude mixture was purified by column chromatography using chloroform:methanol (95:5-80:20) as eluting mixture to get the corresponding product 4. The products reported herein, were characterized by 1H NMR, 13C NMR, and mass spectroscopy. The spectroscopic data of the compounds are in agreement with those reported in the literature.29 Spectral data for 3a29a-d. 1H NMR (400 MHz, CDCl3): δ 1.92-2.14 (m, 4H), 2.14-2.66 (m, 2H), 3.82 (s, 4H), 4.14 (m, 1H), 7.01-7.49 (m, 15H); 13C NMR: δ 29.4, 36.5, 41.4, 62.5, 125.80, 127.40, 128.41, 144.70; MS (ESI): 342 (M+).
  • 46
  • [ 637-50-3 ]
  • [ 100-53-8 ]
  • [ 35906-29-7 ]
YieldReaction ConditionsOperation in experiment
92% With tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 5h; Sealed tube; Irradiation; regioselective reaction;
83% With benzophenone In acetonitrile at 20℃; for 14h; Inert atmosphere; Irradiation; regioselective reaction; General procedure for the synthesis of sulphides 3 General procedure: A mixture of olefin 1 (1 mmol), benzophenone (10 mol%), thiol 2 (1 mmol) and nitrile (3 mL) was stirred at rt under a nitrogen atmosphere and irradiation with visible light (18 W compact fluorescent lamp) for 12-18 h. After completion of reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography using a mixture of hexane/ethyl acetate (4:1) as eluent to afford an analytically pure sample of product 3. All the compounds 3 are known and were characterized by comparison of their spectral data with those reported in the literature.
54% With C36H32IrN4(1+)*F6P(1-); <i>p</i>-toluidine In acetonitrile at 20℃; Irradiation;
  • 47
  • [ 101-39-3 ]
  • [ 637-50-3 ]
  • [ 22436-06-2 ]
  • 48
  • [ 101-39-3 ]
  • [ 637-50-3 ]
  • [ 538-93-2 ]
  • [ 22436-06-2 ]
  • 49
  • [ 637-50-3 ]
  • [ 2926-29-6 ]
  • [ 128271-44-3 ]
YieldReaction ConditionsOperation in experiment
92% With dipotassium peroxodisulfate; silver nitrate In N,N-dimethyl-formamide at 20℃; for 24h;
  • 50
  • [ 3481-09-2 ]
  • [ 637-50-3 ]
  • C17H14ClNO2 [ No CAS ]
  • 51
  • [ 637-50-3 ]
  • [ 103-79-7 ]
YieldReaction ConditionsOperation in experiment
81% With C13H18N4O; iron(II) chloride In acetonitrile 8 Preparation of phenylacetone: The olefin is β-methylstyrene, the ligand is L3, the iron salt is ferrous chloride, and the solvent is acetonitrile. Propiophenone was prepared according to the method of implementation seven, with a yield of 81%.
64% With chloropyridinecobaloxime(III); water; 9‑mesityl-10-methylacridinium perchlorate In acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;
15 %Spectr. With [Ru(2,6-Cl2tpp)Cl2]; 2,6-dichloropyridine N-oxide In chloroform-d1 at 60℃; for 24h; Alkene substrate (0.1 mmol) and internal standard compound trimethylphenylsilicane(5 μL) were dissolved in CDCl3 (0.5 ml) in an NMR tube to record a 1H NMR. Then[RuIV(TDCPP)Cl2] (2.0 mol%) and Cl2pyNO (1.03 equiv) were added and kept themixture at 60 oC. The progress of the reaction was monitored by 1H NMR. Afterdetermination of the product yield by 1H NMR spectroscopy, the product ketone wasseparated by flash chromatography on silica gel.
Multi-step reaction with 2 steps 1: 5Ni(2+)*2C48H26N4O8(4-)*4H2O*O(2-) / acetonitrile / 4 h / 100 °C 2: 5Ni(2+)*2C48H26N4O8(4-)*4H2O*O(2-) / acetonitrile / 24 h / 100 °C
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / Inert atmosphere 2: (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen / dichloromethane / 16 h / 20 °C / 2250.23 Torr
92 %Spectr. With dichloro-acetic acid; bis(dimethylglyoximatodifluoroboryl)cobalt(II); 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; lithium nitrate; water In acetonitrile for 20h; Inert atmosphere; Irradiation;

  • 52
  • [ 637-50-3 ]
  • [ 873-55-2 ]
  • [ 27839-91-4 ]
YieldReaction ConditionsOperation in experiment
85% With heme b; D-glucose; water; oxygen; glucose oxidase at 20℃; for 2h; General procedure for the synthesis of β-ketosulfones General procedure: To a mixture of alkenes/alkynes (0.5 mmol), sodium benzenesulfinate(0.5 mmol), glucose (1.1 mmol) in water (2 ml), hemoproteins(heme concentration: 0.06 mol%), GOX (42 U/ml), was added. The reaction mixture was then stirred at room temperature in a round bottom flask for 2 h, with oxygen added at a rate of 1 mL/min. The reaction was monitored by TLC. When the reaction was complete, the crude mixture was extracted with ethyl acetate. Then the organic phase was dried over sodium sulfate and concentrated under reduced pressure. Finally, the desired product was obtained by flash column chromatography with petroleum ether/ethyl acetate (4/1) as an eluent. All the isolated products were well characterized by their 1H spectral analysis.
82% With dipotassium peroxodisulfate; water at 20℃; for 18h;
  • 53
  • [ 637-50-3 ]
  • [ 1895-39-2 ]
  • trans-1,1-difluoro-2-methyl-3-phenylcyclopropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In tetrahydrofuran at 170℃; for 0.0833333h; Microwave irradiation; Typical Experimental Procedure General procedure: Sodium chlorodifluoroacetate (914 mg 6.0 mmol) wascompletely dissolved in a THF solution (4.0 mL) of alkene(2.0 mmol) and exposed to MW irradiation (using aMilestone MicroSYNTH reactor and Q20 vessel withWeflon button and magnetic stirring bead). Twist control,rotor control, start parameters, and continuous power wereall selected. T2 control was used with 89% stirring. Methodparameters were set at 300 W, 170 °C, 00:05:00). Aftersampling for quantitative NMR studies, the reaction mixturewas diluted with H2O (20.0 mL) and the crude reactionproduct extracted into Et2O (3 × 20.0 mL). The combinedorganic extracts were dried over anhydrous MgSO4 and thesolvent removed in vacuo to yield the crude product as abrown oil. The crude reaction products were purified bycolumn chromatography using 100% hexanes as eluent.
  • 54
  • [ 637-50-3 ]
  • [ 154377-45-4 ]
YieldReaction ConditionsOperation in experiment
94% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In 1,1,2-trichloroethane; toluene at 20℃; for 12h; Inert atmosphere; Asymmetric hydrosilylation using P4 as a ligand in 1,1,2-TCE/toluene (3/1): A solution of polymer ligand P4 (13.3 mg, 2.0 μmol phosphorus atom) in 1,1,2-TCE (0.6 ml) and toluene (.0.2 mL) was stirred for 24 h at 60 °C. To the mixture was added [PdCl(π-allyl)]2 (0.01 M in 1,1,2-trichloroethane, 50 μL, 0.5 μmol), and the solution was stirred for 10 min. Styrene (104.2 mg, 1.0 mmol) and HSiCl3 (0.15 mL, 1.5 mmol) were then added to the mixture. The mixture was stirred for 12h. After the reaction, the mixture was extracted with MeCN × 3, and subjected to bulb-to-bulb distillation, giving the relative hydrosilylation product (225.2 mg, 94% yield).
90% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In 1,1,1-trichloroethane; toluene at 20℃; for 24h; Inert atmosphere; enantioselective reaction;
88% With bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane In chloroform; 1,1,2,2-tetrachloroethane at 20℃; for 24h; Inert atmosphere; enantioselective reaction;
  • 55
  • [ 637-50-3 ]
  • [ 830-43-3 ]
  • N-(2-bromo-1-phenylpropyl)-4-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • 56
  • [ 637-50-3 ]
  • [ 546-89-4 ]
  • [ 21040-45-9 ]
YieldReaction ConditionsOperation in experiment
30%Spectr. With oxygen; palladium diacetate; In acetic acid; acetonitrile; at 80℃; under 3102.97 Torr; for 24h; General procedure: Allylbenzene (132 muL, 1 mmol), <strong>[546-89-4]LiOAc</strong> (130 mg, 3 mmol) and Pd(OAc)2 (10 mg, 5 mol%) were weighed out in a thick-wall pressure tube. 1.2 mL HOAc and 0.8 mL CH3CN were then added. The tube was equipped with a pressure regulator. The tube was charged with 60 psi of O2 following purging and allowed to stir at 80 C overnight. The reaction was then cooled to room temperature and trimethoxybenzene (50 mg, 0.3 mmol) was added as an internal standard. Solvent was then removed by rotovap and the sample was analyzed by 1H NMR spectroscopy. Reactions with other alkene substrates applied the same procedure as allylbenzene.
  • 57
  • potassium iodomethyltrifluoroborate [ No CAS ]
  • [ 292638-84-7 ]
  • [ 300-57-2 ]
  • [ 637-50-3 ]
  • [ 873-49-4 ]
YieldReaction ConditionsOperation in experiment
22%Chromat. With trans-di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium carbonate; tris-(o-tolyl)phosphine; In methanol; N,N-dimethyl acetamide; at 90℃; for 24h;Schlenk technique; General procedure: In the glove box, a 5 ml . Young Schlenk (approximately 10 mL total volume) was equipped with a glass coated st ir bar. In the glove box, base (1.5 equiv ), methylenat ion reagent ( 1 .5 equiv), olefin (1 equiv). and catalyst (5 mol%) were transferred to the vial. A degassed solvent mixture of a polar solvent (16 mL/mmol. substrate) and a ROH solvent (2 mL/mmol substrate) were added and the Schlenk was closed. After transferring the Schlenk outside the glove box, the reaction mixture was heated to 90 C in an oil bath and st irred for 16 h. Then the reaction mixture was ra idly cooled to 0 C in an ice bath. Consecutively undecane (0.4 equiv) as internal standard, EbO (45 ml . mmol substrate) and water (45 ml. /mmol substrate) were then added. The phases were separated and the aqueous phase was extracted with EbO (45 mL/mmol substrate). The combined organic phases were washed w ith brine (45 mL/mmol substrate), dried over MgS04 and analyzed by GC-MS.
  • 58
  • [ 637-50-3 ]
  • [ 5683-31-8 ]
  • trans-(E)-5-methyl-4-phenyl-3-((trimethylsilyl)methylene)dihydrofuran-2(3H)-one [ No CAS ]
  • trans-(Z)-5-methyl-4-phenyl-3-((trimethylsilyl)methylene)dihydrofuran-2(3H)-one [ No CAS ]
  • 59
  • [ 637-50-3 ]
  • [ 1041178-28-2 ]
  • trans-(Z)-5-methyl-4-phenyl-3-(thiophen-3-ylmethylene)dihydrofuran-2(3H)-one [ No CAS ]
  • trans-(E)-5-methyl-4-phenyl-3-(thiophen-3-ylmethylene)dihydrofuran-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
20 % de With 2,6-dimethylpyridine; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; diphenyldisulfane In dichloromethane at 20℃; for 96h; Inert atmosphere; Irradiation; Sealed tube; diastereoselective reaction;
  • 60
  • [ 637-50-3 ]
  • [ 579-07-7 ]
YieldReaction ConditionsOperation in experiment
67% With tert.-butylhydroperoxide; water; tetra-(n-butyl)ammonium iodide In acetonitrile at 90℃; for 12h;
Multi-step reaction with 2 steps 1: oxygen; tetrakis(acetonitrile)copper(I) perchlorate / acetonitrile / 18 h 2: triethylamine / 16 h / 90 °C / Inert atmosphere
  • 61
  • [ 887144-94-7 ]
  • [ 637-50-3 ]
  • [ 128271-44-3 ]
YieldReaction ConditionsOperation in experiment
71% With tris[2-phenylpyridinato-C2,N]iridium(III); dimethyl sulfoxide at 20℃; for 2h; Irradiation; Green chemistry;
  • 62
  • [ 637-50-3 ]
  • [ 1864-94-4 ]
  • [ 56379-64-7 ]
  • 2-methyl-3-phenylpropanoic acid phenyl ester [ No CAS ]
  • 63
  • [ 637-50-3 ]
  • [ 1864-94-4 ]
  • [ 351874-81-2 ]
  • 64
  • [ 637-50-3 ]
  • [ 73183-34-3 ]
  • [ 916658-74-7 ]
YieldReaction ConditionsOperation in experiment
94% With potassium <i>tert</i>-butylate; iron(II) chloride; <i>tert</i>-butyl alcohol In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;
87% Stage #1: bis(pinacol)diborane With bis(1,5-cyclooctadiene)nickel(0); tricyclohexylphosphine In toluene at 20℃; for 0.166667h; Schlenk technique; Sealed tube; Inert atmosphere; Stage #2: 1-phenylpropene With water In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere; General Procedure for Ni-Catalyzed Hydrobolation of Olefins General procedure: A 20-mL sealed Schlenk tube containing a magnetic stir bar was charged with B2pin2 (38.1 mg, 0.15 mmol), Ni(cod)2 (2.8 mg, 10.0 µmol), PCy3 (5.6 mg, 20.0 µmol) and 1.0 mL of dry toluene. The mixture was stirred at room temperature for 10 min then added olefins (0.10 mmol) and H2O (3.6 mg, 0.20 mmol). The reaction vessel was sealed then heated at 100 °C for 18 h. The resulting solution was cooled to room temperature, extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 , filtered and concentrated under reduced pressure. The crude product was purified by recycle GPC.
85% With methanol; bis(1,5-cyclooctadiene)nickel(0); tri-tert-butyl phosphine In toluene at 75℃; for 10h;
  • 65
  • [ 637-50-3 ]
  • [ 55962-05-5 ]
  • trans-2-methyl-3-phenyl-1-tosylaziridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With [Cu(N,N'-bis(4-hydroxysalicylidene)phenylene-1,2-diamine)] immobilized on modified multi-wall carbon nanotubes In acetonitrile at 25℃; for 3h; General procedure for aziridination of styrene General procedure: [Cu((OH)2-salophen)]MWNTs] (5.6 mol%), styrene (0.56 ml,5 mmol) and PhI = NTs (0.372 g, 1 mmol) were added to acetonitrile (3 ml) and the reaction mixture was stirred at room temperature.The reaction was monitored by disappearance of the PhI = NTs from the reaction mixture. After completion of the reaction, the catalyst was filtered and the filtrate was concentrated and purified by column chromatography (hexane/ethyl acetate, 95/5, v/v) to afford pure product as white solid
  • 66
  • [ 637-50-3 ]
  • 1-phenyl-2-nitroprop-1-ene [ No CAS ]
  • [ 58321-79-2 ]
YieldReaction ConditionsOperation in experiment
78% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; dipotassium peroxodisulfate; sodium nitrite In 1,2-dichloro-ethane at 100℃; for 24h; Sealed tube; stereoselective reaction; General procedure for the synthesis of compounds 2 and 4 General procedure: To a 25 mL sealed tube were added alkenes 1 or 3 (0.5mmol) with NaNO2 (1.5 equiv.), K2S2O8 (2.0 equiv.), TEMPO (1.2 equiv.) and ClCH2CH2Cl (2 mL). The reaction mixture was stirred at 100 oC for 24 h. After the reaction was finished, the reaction was cooled to room temperature. Dichloromethane (2 mL) and water (5 mL) were added. The organic layer was separated, and the aqueous phase was extracted with dichloromethane (5 mL × 3). The combined organic layers were dried with anhydrous Na2SO4, filtered. After evaporating the solvent in vacuum, the residue was purified by column chromatography eluting with PE/EtOAc to obtain the pure nitroalkenes 2 or 4.
  • 67
  • [ 637-50-3 ]
  • [ 109-89-7 ]
  • [ 90-84-6 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 1-phenylpropene With N-Bromosuccinimide; water at 80℃; for 1.2h; Inert atmosphere; Stage #2: diethylamine In acetone at 20℃; Inert atmosphere;
  • 68
  • [ 637-50-3 ]
  • (1R*,1S*)-1-fluoro-2-iodo-1-phenylpropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dichloro bis(acetonitrile) palladium(II); 1-fluoro-3,3-dimethyl-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole In chloroform-d1 at 40℃; for 18h;
  • 69
  • [ 5765-65-1 ]
  • [ 637-50-3 ]
  • [ 602-94-8 ]
  • 2-morpholino-1-phenylpropyl 2,3,4,5,6-pentafluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With copper diacetate In 1,2-dichloro-ethane at 80℃; for 0.25h; regioselective reaction; Established standard procedure for olefin oxyamination reaction General procedure: To a 1 Dram vial with Teflon-coated micro stir bar was added carboxylic acid 1 (1.2 mmol, 3 equiv), O-benzoylhydroxylamine 3 (0.4 mmol, 1 equiv), and copper(II) acetate (0.08 mmol, 0.2 equiv), followed by addition of anhydrous 1,2-dichloroethane (2.0 mL) and olefin 2 (1.2 mmol, 3 equiv). The resulting solution was stirred at 80 °C for 15 min until the consumption of O-benzoylhydroxylamine 3 (monitored by TLC). The resulting reaction mixture was cooled to room temperature and filtered through a plug of activated, neutral Al2O3 (Brockman grade I, 58-60Å). The filtrate was concentrated under reduced pressure, providing the crude reaction mixture. The crude reaction mixture was purified by silica column chromatography unless otherwise noted.
  • 70
  • [ 637-50-3 ]
  • [ 14229-93-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; water / 2 h / 80 °C / Inert atmosphere; Green chemistry 2: water / 2 h / 80 °C / Inert atmosphere; Green chemistry
  • 71
  • [ 637-50-3 ]
  • [ 4559-70-0 ]
  • [ 784082-51-5 ]
YieldReaction ConditionsOperation in experiment
70% With manganese triacetate In methanol at 30℃; for 1h; 2.1 General procedure for the preparation of 2-(diphenylphosphoryl)-1-arylethanones 3 General procedure: Typical procedure for the preparation of 2-(diphenylphosphoryl)-1-phenylethanone (3a). To a solution of methanol (10 mL), styrene (0.11 g, 1.0 mmol) and diphenylphosphine oxide (0.40 g, 2.0 mmol) was added Mn(OAc)3 (0.54 g, 2.0 mmol) over 30 min at 30 °C, and the mixture was stirred for another 30 min to complete the reaction. Then, the solvent was removed under vacuum. To the residue was added water (20 mL) and extracted with ethyl acetate (10 mL*3). The combined organic fractions were dried over anhydrous Na2SO4, and concentrated under vacuum to yield the crude product, which was purified by column chromatography (silica gel, petroleum ether/EtOAc/CH2Cl2 (10:1:1)) to give pure 2-(diphenylphosphoryl)-1-phenylethanone (3a).
70% With manganese triacetate In methanol at 30℃; for 1h; Representative Procedure for the Preparation of β-Hydroxyphosphine oxides 3 General procedure: To a stirring solution of alkene (1.0 mmol) and diphenylphosphine oxide (2.0 mmol) in MeOH (5 mL) at 30 °C was added Mn(OAc)3 (2.0 mmol) in portions over 30 minutes. After the completion of reaction as indicated by TLC (about 30 minutes later), the mixture was cooled and the solvent was removed under vacuum. The pure product 3 was obtained by column chromatography on silica gel using petroleum ether/EtOAc/CH2Cl2 (4:1:1) as eluent.
  • 72
  • [ 637-50-3 ]
  • [ 104-88-1 ]
  • 1-(4-chlorophenyl)-2-phenylbutan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With [(C6H6)(PCy3)(CO)RuH]+*BF4 In toluene at 110℃; for 16h;
  • 73
  • [ 637-50-3 ]
  • [ 1678-92-8 ]
YieldReaction ConditionsOperation in experiment
>99 %Chromat. With hydrogen In 1,3,5-trimethyl-benzene at 120℃; for 18h; Glovebox; Autoclave;
  • 74
  • [ 637-50-3 ]
  • [ 55962-05-5 ]
  • [ 6971-74-0 ]
YieldReaction ConditionsOperation in experiment
39% General procedure: To a solution of stilbene 1a (0.090 g, 0.50 mmol) and PhI=NTs (0.746 g, 2.0 mmol) in CHCl3 (1.0 mL) was added PdCl2 (0.008 g, 0.05 mmol) at rt. After the reaction mixture was stirred at rt for 6h, a solution of FeCl2 (0.006 g, 0.05 mmol) and pyridine (0.016 mL, 0.20 mmol) in CHCl3 (1.0 mL) was added. Upon stirring at rt for 40 h, the crude product was concentrated and purified by flash chromatography (silical gel, EtOAc/MeOH 40/1) to give amide 4a as a white solid .
  • 75
  • [ 637-50-3 ]
  • [ 64-19-7 ]
  • [ 21040-45-9 ]
YieldReaction ConditionsOperation in experiment
61% With Pd-TiO2; oxygen; sodium acetate In dimethyl sulfoxide at 90℃; for 28h; Sealed tube; Green chemistry; regioselective reaction; 2.3.1. A typical procedure for catalytic reactions General procedure: A glass tube was charged with a stirring bar, allylbenzene (1mmol),catalyst (Pd 5 mol%), NaOAc (1 mmol), solvent (total amount of AcOH and DMSO was 2.0 mL), and sealed with an O2 balloon. The reaction was conducted at 90 °C for 28 h. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was analyzed by GC using tridecane as an internal standard.
  • 76
  • [ 637-50-3 ]
  • [ 108-98-5 ]
  • [ 82482-00-6 ]
YieldReaction ConditionsOperation in experiment
68% With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-fluorobis(benzenesulfon)imide In toluene at 20℃; Schlenk technique; Inert atmosphere;
24% With tert.-butylhydroperoxide; methanesulfonic acid In decane; acetonitrile at 40℃; diastereoselective reaction; General procedure: General procedure: To a 1 mL screw cap vial charged with a magnetic stirring bar, dry acetonitrile (0.5ml), the olefin substrate (0.5 mmol, 1 equivalent), the thiol substrate (1.0 mmol, 2equiv.) and tBuOOH (5.5M solution in decane, 1.5 mmol, 3 equiv.) were added in thatorder. To the solution, methanesulfonic acid (3.55 μL, 10 mol%) was added and the reaction mixture was heated at 40°C (in an aluminum heating block) and stirred at 300 rpm. The vials were closed and only contained a small headspace of air, but nospecial treatment was necessary to exclude air or moisture. The reaction mixtures were analyzed by thin-layer-chromatography in order to determine the time when full conversion was reached. The reaction mixture was diluted, a small amount of silica was added and the solvent was removed under vacuum. The resulting powder was purified by column chromatography on silica gel using mixtures of hexane and acetone to afford the desired product.
  • 77
  • [ 524-38-9 ]
  • [ 637-50-3 ]
  • C17H15NO4 [ No CAS ]
  • C17H15NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide; oxygen In decane; 1,2-dichloro-ethane at 20℃; for 22h; Overall yield = 99 %; Optical yield = 50 %de; 1 Typical procedure for the synthesis of product 3 General procedure: To a solution of N-hydroxyphthalimide (2, 0.3 mmol, 48.9 mg) in DCE (3.0 mL) was added styrene (1a, 0.6 mmol), 10% TBHP (5-6 M in decane). The flask was evacuated and back filled with O2 for three times. The reaction mixture was then stirred for 24 h at room temperature. After the reaction, the resulting mixture was quenched with water and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. Purification of the crude product by flash column chromatography afforded the product 3a (petroleum ether/ethyl acetate as eluent (6:1)).
Stage #1: N-hydroxyphthalimide; 1-phenylpropene With tris(2,2,6,6-tetramethyl-3,5-heptanedionato) manganese (III); oxygen In acetonitrile at 20℃; for 1h; Stage #2: With dimethylsulfide Overall yield = 64 percent; Overall yield = 2.9 g;
  • 78
  • [ 637-50-3 ]
  • [ 81290-20-2 ]
  • [ 128271-44-3 ]
YieldReaction ConditionsOperation in experiment
74% With oxygen; silver fluoride In N,N-dimethyl-formamide at 20℃; Schlenk technique;
  • 79
  • [ 637-50-3 ]
  • [ 90-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water / 1 h / 60 °C / Green chemistry 2: water / 24 h / 20 °C
  • 80
  • [ 637-50-3 ]
  • [ 133745-75-2 ]
  • N,N'-(1-phenylpropane-1,2-diyl)bis(N-(phenylsulfonyl)benzenesulfonamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,2,6,6-tetramethylheptane-3,5-dione; 1,1,1,2,2,2-hexamethyldisilane; tetrabutyl-ammonium chloride; copper(l) chloride In acetonitrile at 70℃; for 2h; Schlenk technique; Inert atmosphere; diastereoselective reaction; Representative procedure for the diamination of alkenes : (Table 2) General procedure: An oven-dried, 5 mL Schlenk flask equipped with a stir bar was place under an atmosphere of N2. CuCl (2.45 mg, 0.025 mmol%, 5 mol%) and dissolved in 0.5 mL fresh distilled CH3CN. 2,2,6,6-Tetramethyl-5-heptanedione (TMHD, 4.7 mg, 5.7μL, 0.025 mmol%, 5 mol%), 2,2,6,6-tetramethyl piperidine N-oxy radical (TEMPO, 11.7 mg, 0.075 mmol, 15 mol%) and hexamethyldisilane (150 mg, 154 μL, 0.75 mmol%, 1.5 equiv) were sequentially added to the above solution and stirred for 20 min. N-Fluorobenzenesulfonimide (472 mg, 1.5 mmol, 3.0 equiv) and styrene (57 μL, 0.5 mmol, 1.0 equiv) were dissolved in 0.5 mL fresh distilled CH3CN and added to the flask via a syringe at room temperature under nitrogen atmosphere. The resulting mixture was heated to 70 °C on a preheated oil spot, and the reaction progress was monitored by TLC analysis. After completion of the reaction, the mixture was cooled to 0°C, and quenched with 2 mL ofice-cold sat. NaHCO3 (aq). The remaining material was extracted three times with ethyl acetate (10mL) and the organic layer was dried with Na2SO4, and filtrated. Evaporation of the organic solvent and the resulting mixture was purified by column chromatography on silica gel (hexane-AcOEt 7:1) to afford the aminoalcohol 1a (247 mg, 71% yield) as a white solid.
  • 81
  • [ 637-50-3 ]
  • [ 7677-24-9 ]
  • [ 4559-70-0 ]
  • 3-(diphenylphosphoryl)-2-phenylbutanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; manganese(II) acetate In acetone at 50℃; Inert atmosphere; 18.1; 18.2; 18.3 Example 18: Synthesis of 2-phenyl-3-diphenylphosphinylidene nitrile The reaction procedure is as follows: β - methylstyrene and diphenylphosphine oxide as raw materials.Β - methylstyrene (0.047 g, 0.4 mmol), diphenylphosphine oxide (0.162 g, 0.8 mmol), trimethylcyanosilane (0.079 g, 0.8 mmol), CuI (0.076 g, 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and acetone (3 mL) under argon at 50 ° C;TLC tracks the reaction until it ends completely;The crude product obtained after the completion of the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1: 1) to give the desired product (yield 80%).
80% With copper(l) cyanide; manganese(III) triacetate dihydrate In N,N-dimethyl-formamide at 20℃; for 3h; Schlenk technique; Inert atmosphere;
  • 82
  • [ 637-50-3 ]
  • [ 65-85-0 ]
  • [ 5320-75-2 ]
YieldReaction ConditionsOperation in experiment
86% With di-tert-butyl peroxide; [HSItBu][FeBr4] In neat (no solvent) at 110℃; for 16h; regioselective reaction; General Procedure for the synthesis of 7a General procedure: To a reaction vessel was added 2 (13.9 mg, 0.025 mmol), 4-methoxybenzoic acid (76.1 mg, 0.5 mmol), DTBP (187 μL, 1.0 mmol), cyclohexene (1.0 mL) and ethyl acetate (0.5 mL) under air. The mixture was stirred for 24 h at 110 °C. After cooling to room temperature, ethyl acetate (10 mL) was added, and the mixture was filtered. The GC yield of the desired product was determined using GC analysis, with n-hexadecane as an internal standard. Purification of the crude mixture by column chromatography on silica gel using ethyl acetate/petrol ether (60-90 °C) as eluent gave the isolated yield of desired product.
  • 83
  • [ 637-50-3 ]
  • [ 762-04-9 ]
  • [ 10409-56-0 ]
YieldReaction ConditionsOperation in experiment
70% With copper(ll) sulfate pentahydrate In acetonitrile at 60℃; for 2h; 11 Example 11 Diethyl- (1-methyl-2-phenyl) -2-oxo) phosphonate β-methyl styrene (0.118 g, 1 mmol) or α-methylcinnamic acid (0 · 162 g, 1 mmol), diethyl H-phosphite (0.276 g, 2 mmol), CuSO4.5H2O (0 · 026g, 0 · 1mmol), acetonitrile 10mL 25mL three-necked flask was heated to 60 °C in an oil bath at this temperature to continue the reaction 2h TLC plate was used to detect the progress of the reaction until the reaction is complete, with two The organic phase was combined and dried over Na2SO4. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography (petroleum ether / ethyl acetate, V / V = 1: 1) to give the title compound as a yellow oil , Yield 70%.
62% With pyridine; manganese(III) acetylacetonate In acetonitrile at 20℃; for 24h; Representative Procedure for Mn(acac)3-Catalyzed Oxophosphorylation Reaction General procedure: A 10 mL test tube was charged with 1-methyl-4-vinylbenzene (1a) (118.2 mg, 1.00 mmol),MeCN (1.0 mL), diethyl phosphonate (2) (258 μL, 2.00 mmol) and pyridine (243 μL, 3.00 mmol). The solution was stirredat room temperature in air (open flask). After 21 h, the reaction was quenched with saturated aqueous NaCl solution(0.5 mL). The resulting mixture was extracted with ethyl acetate (3×1.0 mL). The combined organic phases were washed with brine (1.0 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained crude material was purified by column chromatography (silica gel,hexane : EtOAc=1 : 1) to afford 3a (221.5 mg, 0.82 mmol, 82%).
42% With iron(III) chloride; di-tert-butyl peroxide; triethylamine; copper(l) chloride In dimethyl sulfoxide at 90℃; for 15h; Inert atmosphere; Green chemistry;
41% With iron(III) chloride; triethylamine; copper dichloride In dimethyl sulfoxide at 60℃; for 24h;

  • 84
  • [ 637-50-3 ]
  • 2-bromo-1-phenyl-1-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With water; hydrogen bromide In dimethyl sulfoxide at 60℃; for 12h; Schlenk technique; 17 Example 17 Synthesis of 2-bromo-1-phenyl-1-propanol Take a 25 mL Schlenk reaction tube, add 59 mg of m-methylstyrene,48% hydrobromic acid in water, 2 mL of dimethylsulfoxide, and the mixture was stirred at 60 ° C for 12 hours. After the completion of the reaction, 15 mL of ethyl acetate was added to quench the reaction, and the mixture was washed with 5 mL of brineThe organic phase was separated and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined and chromatographed to give 2-bromo-1- (3-methyl-Phenyl) -ethanol, 87 mg, yield 81%.
  • 85
  • [ 21087-29-6 ]
  • [ 1450-14-2 ]
  • [ 637-50-3 ]
  • [ 40595-34-4 ]
YieldReaction ConditionsOperation in experiment
45% With DMA coordinated palladium element containing nanoparticles In N,N-dimethyl acetamide at 100℃; for 16h; Schlenk technique; Inert atmosphere; 3 To Schlenk substituted with argon, 0.5 mmol of cinnamyl chloride, 2.0 mmol of hexamethyldisilane, synthesized palladium element-containing nanoparticles (material amount of palladium element: 0.001 mmol, amount of substance of palladium element to cinnamyl chloride: 0.2 mol%), 1 mL of dimethylacetamide The reaction was carried out by heating and stirring at 100 ° C. for 16 hours. The reaction was carried out in the same manner as in Example 1 except that the amount of palladium element-containing nanoparticles was changed to 0.0005 mmol (0.1 mol%).
  • 86
  • [ 637-50-3 ]
  • [ 698-87-3 ]
YieldReaction ConditionsOperation in experiment
87% With water; diphenyldisulfane; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; regioselective reaction;
  • 87
  • [ 637-50-3 ]
  • [ 124-38-9 ]
  • [ 1009-67-2 ]
  • [ 90-27-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-phenylpropene With 9-borabicyclo-[3.3.1]nonane dimer In 1,4-dioxane at 65℃; for 16h; Stage #2: carbon dioxide With copper(l) iodide; 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene hydrochloride; cesium fluoride at 120℃; for 16h; Stage #3: With hydrogenchloride In water
  • 88
  • [ 637-50-3 ]
  • [ 200341-03-3 ]
  • C26H23NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 2,4,6-tris(4-methylphenyl)pyrylium tetrafluoroborate In dichloromethane at 20℃; for 12.5h; Inert atmosphere; Irradiation; 7 Example 7 To a 7 mL round bottom flask, 74 mg (0.3 mmol)N-phenyl-α-naphthyl nitrone,53 mg (0.45 mmol)) of β-methylstyrene, 1.2 mg (0.0075 mmol) of photocatalyst and 5 mL of methylene chloride were added and the mixture was stirred for 30 minutes. After placing under blue LEDs, the mixture was irradiated with light for 12 hours at room temperature. After the reaction was completed, the reaction solvent was concentrated by rotary evaporator and dried. The residue was purified by silica gel column chromatography using petroleum ether: ethyl acetate in a volume ratio of 45: 1 as a eluent to give a corresponding Replacing isoxazolidine derivatives, the reaction formula is:The product has a purity of 99% and a yield of 70%.
  • 89
  • [ 637-50-3 ]
  • 1-cyclohexyl-N-phenylmethanimine oxide [ No CAS ]
  • C22H27NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With 2,4,6-tris(4-methylphenyl)pyrylium tetrafluoroborate In dichloromethane at 20℃; for 19.5h; Inert atmosphere; Irradiation; 8 Example 8 Into a 7 mL round bottom flask, 61 mg (0.3 mmol)N-phenyl-α-cyclohexylnitrone,53 mg (0.45 mmol)) of β-methylstyrene, 1.2 mg (0.0075 mmol) of photocatalyst and 4 mL of methylene chloride were added and the mixture was stirred for 30 minutes under nitrogen. The mixture was placed under blue LEDs for 19 hours at ambient temperature. After the reaction was completed, the reaction solvent was concentrated by rotary evaporator to dryness, and then a petroleum ether: ethyl acetate solution with a volume ratio of 50: 1 was used as the eluent. The residue was purified by silica gel column chromatography to obtain the corresponding Replacing isoxazolidine derivatives, the reaction formula is:The product had a purity of 99% and a yield of 55%.
  • 90
  • [ 637-50-3 ]
  • [ 139174-27-9 ]
  • C22H20FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 2,4,6-tris(4-methylphenyl)pyrylium tetrafluoroborate In dichloromethane at 20℃; for 12.5h; Inert atmosphere; Irradiation; 9 Example 9 To a 7 mL round bottom flask, 65 mg (0.3 mmol)N-phenyl-α-2-fluorophenyl nitrone,53 mg (0.45 mmol)) of β-methyl styrene, 1.2 mg (0.0075 mmol) of photocatalyst and 4 mL of methylene chloride were added, the mixture was stirred for 30 minutes and then placed under blue LEDs. The mixture was irradiated with light at room temperature for 12 hours. After the reaction was completed, the reaction solvent was concentrated by rotary evaporator to dryness. The mixture was further purified by silica gel column chromatography using petroleum ether: ethyl acetate (50: 1 by volume) as eluent to give a corresponding Replacing isoxazolidine derivatives, the reaction formula is:The product had a purity of 99% and a yield of 87%.
  • 91
  • [ 637-50-3 ]
  • [ 201024-81-9 ]
  • C22H21NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 2,4,6-tris(4-methylphenyl)pyrylium tetrafluoroborate In dichloromethane at 20℃; for 12.5h; Irradiation; Inert atmosphere; 1 Example 1 Into a 7 mL round bottom flask, 59 mg (0.3 mmol) diphenylnitrone was added,53 mg (0.45 mmol) of β-methylstyrene, 1.2 mg (0.0075 mmol) of photocatalyst and 4 mL of methylene chloride were added, the mixture was stirred for 30 minutes and then placed under blue LEDs. The mixture was irradiated with light at room temperature for 12 hours. After the reaction was completed, the reaction solvent was concentrated by rotary evaporator to dryness, and then a petroleum ether: ethyl acetate solution with a volume ratio of 50: 1 was used as the eluent. The residue was purified by silica gel column chromatography to obtain the corresponding Replacing isoxazolidine derivatives, the reaction formula is:The product had a purity of 99% and a yield of 85%.
  • 92
  • [ 637-50-3 ]
  • [ 98-74-8 ]
  • 1-((1-chloro-1-phenylpropan-2-yl)sulfonyl)-4-nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 20℃; for 4h; Irradiation; Inert atmosphere; chemoselective reaction; Preparation of products General procedure: A 10 mL reaction vessel with a magnetic stirring bar wasequipped with sulfonyl chloride(0.5 mmol), alkene (0.5 mmol), Ru(bpy)3Cl2·6H2O (1mol%), and acetonitrile (2 mL). The mixture was irradiated with a blue LED (5 W)and stirred under at r.t. in an air atmosphere for 4h. The distance of the reaction vialfrom the light is about 2 centimeter. After the reaction, the solvent was removed underreduced pressure. Purification of the crude product was achieved by flash columnchromatography using petrol ether/ethyl acetate (6:1~10:1) as eluent.
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