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CAS No. :612-00-0 MDL No. :MFCD00055631
Formula : C14H14 Boiling Point : -
Linear Structure Formula :C6H5CHCH3C6H5 InChI Key :BSZXAFXFTLXUFV-UHFFFAOYSA-N
M.W : 182.26 Pubchem ID :11918
Synonyms :

Safety of [ 612-00-0 ]

Signal Word:Danger Class:9
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 UN#:3082
Hazard Statements:H302-H319-H372-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 612-00-0 ]

* 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 [ 612-00-0 ]

[ 612-00-0 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 530-48-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
100% With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 60℃; for 24h; chemoselective reaction;
100% With water monomer for 6h; Milling; Green chemistry;
100% With <SUP>i</SUP>Pr-amboxCoCl<SUB>2</SUB>; hydrogen; sodium triethylborohydride In toluene at 0 - 20℃; Sealed tube; 3. Data for the Hydrogenation of Alkenes General procedure: For convenience, reactions were set up in a nitrogen-filled glove box. An oven-dried 1-dram vial equipped with a Teflon-coated stir bar was charged with iPramboxCoCl2 (0.0125 mmol, 5.0 mg) and alkene (0.25 mmol). The vial was capped with a septa and brought outside the glovebox. Outside the glovebox, a balloon with hydrogen was added and the system was purged with H2 three times. Next, toluene (0.5 mL) was added and the reaction mixture was cooled to 0 °C. To the cooled solution, NaBEt3H (1 M in toluene, 0.0375 mmol, 37.5 μL) (drop-wise addition) was added. Upon addition of NaBEt3H, an immediate color change was observed from blue to brown. After complete addition, the reaction mixture was kept at 0 °C for ca. 5 min and then the ice bath was removed, and reaction mixture was stirred at room temperature overnight. Next, the reaction was quenched by the addition of pentane (2-3 mL). The mixture was filtered through a pad of celite, washed with pentane, and the filtrate was concentrated to afford crude material.
99% With hydrogen tetrafluoroborate; dicobalt octacarbonyl; p-dodecylbenzenesulfonic acid sodium salt In benzene at 55℃; for 4h;
99% With 10% Pd on charcoal; diludine In ethanol for 4h; Reflux;
99% With Pd(SIPr)(PCy3); hydrogen In methanol at 20℃; for 24h;
99% With 4,4'-di-tert-butylbiphenyl; lithium; isopropanol; nickel (II) chloride In tetrahydrofuran at 20 - 76℃; Inert atmosphere; chemoselective reaction;
99% With hydrogen; palladium diacetate; pyrographite In tetrahydrofuran; methanol at 25℃; for 12h;
99% With borane-ammonia complex; Pd(SIPr)(PCy3) In isopropanol at 50℃; for 16h; Inert atmosphere; Glovebox;
99% With 1,3,5-trimethyl-1,4-cyclohexadiene; bis(trifluoromethanesulfonyl)amide In dichloromethane at 20℃; for 12h; Schlenk technique;
99% With palladium 10% on activated carbon; hydrogen at 20℃; for 18h; Sealed tube;
99% With ethanol; (BQ‑NCOP)IrHCl; sodium tertiary butoxide at 60℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube;
99% Stage #1: 1,1-Diphenylethylene With lithium triethylhydroborate; cobalt(II) dibromide In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: With hydrogen In tetrahydrofuran at 20℃; for 3h;
99% With cyclohexa-1,4-diene; C24H72Ba2N4Si8 In hexadeuterobenzene at 60℃; for 1.5h; Inert atmosphere; Schlenk technique; Sealed tube;
99% With 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthenecobalt(II) dibromide; hydrogen; lithium triethylhydroborate In tetrahydrofuran at 20℃; for 3h;
99% With 5%-palladium/activated carbon; hydrogen In methanol at 30℃; for 12h;
99% With 5%-palladium/activated carbon; hydrogen In methanol at 30℃; for 12h; Sealed tube;
99% With Pd/C; C24H16N2O4 In ethanol at 50℃; for 18h; Glovebox;
99% With palladium on activated charcoal; hydrogen In methanol at 30℃; for 12h;
98% With gallium(I) tetrachlorogallate(III); cyclohexa-1,4-diene In toluene at 110℃; for 1h; Inert atmosphere;
97% With 1,3,5-trimethyl-1,4-cyclohexadiene; tris(pentafluorophenyl)borate at 20℃; for 8h; Glovebox; Inert atmosphere;
97% With indium(III) bromide; cyclohexa-1,4-diene In 1,2-dichloro-ethane at 80℃; Sealed tube; Inert atmosphere;
96% With iodine; hypophosphorous acid In glacial acetic acid for 24h; Heating;
96% With triethylsilane; 4-Fluorothiophenol; fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate at 25℃; for 1h; chemoselective reaction; General Procedure for Olefin Transfer-Hydrogenation. General procedure: To a solution of silane(1.0 Eq), RH (R = Ar2N, ArS, ArO, ArCO2) (1.0 Eq) and olefin (1.0-1.2 Eq) wasadded the [(C6F5)3PF][B(C6F5)4] (1.5 mol%) in C6D5Br or CD2Cl2 (0.5 M) at 25 °C. The reaction was monitored by NMR or TLC until completion. Yieldwas determined by 1H-NMR spectroscopy. For isolated yields, the reactionwas quenched with a diluted solution of NaHCO3 and the mixture wasextracted with CH2Cl2. The organic solution was dried over MgSO4, filtered,and evaporated. The crude was diluted with hexane and filtered over silica gel; products were eluted with hexane and Et2O for dibutyl 2-methylenesuccinate. The quality of the catalyst is again essential for the successful completion of the reaction
96% With sodium tetrahydridoborate; di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; water monomer In toluene Sealed tube; Molecular sieve;
95% With tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide electrochemical reduction;
95% With aluminum(III) oxide; sodium tetrahydridoborate In hexane at 40℃;
95% With methanol; formic acid; water monomer In ethyl acetate at 25℃; for 4h; Irradiation; Inert atmosphere;
95% Stage #1: 1,1-Diphenylethylene With sodium triethylborohydride In tetrahydrofuran at 70℃; for 12h; Stage #2: With methanol In tetrahydrofuran
94% With methanol In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 18h; Ambient temperature;
94% With sodium tetrahydridoborate; water monomer In toluene at 100℃; for 22h;
94% With 1,4-dioxane; di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium; 1,2-bis-(dicyclohexylphosphino)ethane at 130℃; for 3h; Inert atmosphere; Sealed tube; chemoselective reaction;
93% With palladium on activated charcoal; tetrabutylammonium bromide; water monomer; sodium hydroxide; silicon at 100℃; for 24h;
93% With bis[chlorido(η2,η2-cycloocta-1,5-diene)rhodium(I)]; tetrahydroxydiborane; water monomer; triethylamine In tetrahydrofuran at 30℃; for 12h; Schlenk technique; Inert atmosphere;
93% With water monomer; palladium diacetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere; 24 Replace the gas atmosphere in the Shrek tube with a nitrogen atmosphere, add 1,1-diphenylethylene 0.25 mmol, palladium acetate 0.00125 mmol, methylene chloride 0.5 mL, water 0.275 mmol, and add pinacol borane 0.275 mmol with stirring After 12 hours of reaction at room temperature, the reaction solution obtained after the completion of the reaction was subjected to column chromatography, and the target product obtained in 93% yield was a colorless liquid.
93% With water monomer; palladium diacetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;
92% With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;
92% With tetrahydroxydiborane; palladium 10% on activated carbon; water monomer In dichloromethane at 20℃; for 60h; Inert atmosphere;
92% With 1-methyl-4-isopropyl-1,3-cyclohexadiene; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 16h; Glovebox; Inert atmosphere;
91% With C48H69N4NiOPSi2; hydrogen In hexadeuterobenzene at 20℃; for 48h; Schlenk technique; Sealed tube;
91% With boron trifluoride diethyl ether complex; (1,4-dihydro-[1,1'-biphenyl]-3-yl)trimethylsilane In dichloromethane at 20℃; for 12h; regioselective reaction;
90% With (BrC6H6)3N(+)*SbCl6(-); bis-tri-n-butylstannane In dichloromethane at 0℃; for 1h; other alkenes and dienes; var. hydrogen-transfer agents; var. time;
90% With bis-tri-n-butylstannane; tris(4-bromophenyl)ammoniumyl hexachloroantimonate In dichloromethane at 0℃; for 1h; other substituted olefins;
90% With FeH(CO)2(P(C6H5)3) In benzene for 0.25h; Ambient temperature;
90% With bis-tri-n-butylstannane; tris(4-bromophenyl)ammoniumyl hexachloroantimonate In dichloromethane at 0℃; for 1h;
90% With (BrC6H5)3N(+)*SbCl6(-); bis-tri-n-butylstannane In dichloromethane at 0℃; for 1h;
90% With acridane derivative; trifluoroacetic acid In dichloromethane for 24h; Ambient temperature;
90% With chlorotriisopropylsilane; diphenyl(pentafluorophenyl)phosphonium tetrakis(perfluorophenyl)borate In dichloromethane at 50℃; for 18h; Inert atmosphere; Schlenk technique; 2.4.6. General experimental procedure for the hydrogenation reaction General procedure: A reaction tube with a Teflon cap was charged with equimolar(0.1 mmol) amounts of olefin and triisopropylsilane. Adichloromethane solution of 10 mol% catalyst was added to the tube and the mixture was heated at 50 °C for 18 h. The reactionmixture was taken in volumetric flask and diluted with DCM. Thediluted solution was analysed by GC-MS.
89% With cyclohexa-1,4-diene; C12H12N3(1+)*C24BF20(1-) In dichloromethane at 20℃; for 24h;
87% With hydrogen; C48H58N4NiSi2 In hexadeuterobenzene at 20℃; for 18h;
85% With water monomer; potassium ethylxanthate In N,N-dimethyl-formamide at 130℃; for 24h;
85% With hydrogen; magnesium; N<SUP>1</SUP>,N<SUP>2</SUP>-bis(2,6-diisopropylphenyl)ethane-1,2-diimine; cobalt(II) dibromide In tetrahydrofuran at 20℃; for 24h;
84% With dichloro(p-cymene)ruthenium(II) dimer; dimethylamine borane In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Sealed ampoule; Representative procedure for metal-catalysed transfer hydrogenation General procedure: To an oven dried, argon purged, ampoule containing [Ru(p-cymene)Cl2]2 (15.3 mg, 0.05 mmol, 2.5 mol%), substrate (1 mmol) and dry thf (to make a total of 3 mL), a solution of dimethylamine borane in thf was added. The ampoule was sealed and heated at 70 °C for 24 hours then cooled to room temperature.
83% With ammonia; lithium perchlorate In acetonitrile at 20℃; Electrochemical reaction;
80% With cyclohexa-1,4-diene; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylideneZnC6F5][B(C6F5)4] In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;
80% With formic acid; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N1,N1']bis[2-(2-pyridinyl-N)phenyl-C]iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In methanol; water monomer at 20℃; for 24h; Irradiation;
77% With hydrogen In toluene at 100℃; for 18h; Autoclave;
75% With C7H14N3(1+)*Cl(1-); sodium triethylborohydride; cobalt(II) chloride In tetrahydrofuran at 60℃; for 16h; Autoclave;
67% With hydrazine hydrate monohydrate In ethanol Heating;
55% With 1-Benzyl-1,4-dihydronicotinamide In methanol for 1h; Irradiation;
55% With n-Pentane for 6h; Milling;
45% With C51H71CoN4O14(1+)*ClO4(1-); trifluoroacetic acid In acetonitrile at 20℃; Electrolysis; Inert atmosphere; 4.3 General bulk electrolysis General procedure: The controlled-potential electrolysis of the alkene was carried out in a divided cell equipped with a carbon felt cathode and a zinc plate anode (1×3cm2) at-0.7V vs. Ag/AgCl in the presence of 1at room temperature in 0.1M n-Bu4NClO4 containing acetonitrile. The applied potential between the working and reference electrodes during the electrolysis was maintained constant using a Hokuto Denko HA BF-501A potentiostat, and the electrical quantity was also recorded by it. The concentrations of the catalyst and substrate were 5.0×10-4M and 5.0×10-2M, respectively. After the electrolysis, the electrolyte solution was passed through silica gel with the CHCl3 eluent, then analyzed by GC-MS. Authentic samples of the products from the catalytic reactions (Tables1 and 2) except for those listed below were purchased from Aldrich or Tokyo Kasei Kogyo (TCI). The 2,3-diphenylhexanes (racemic and meso) (DH) were synthesized by reported methods [30], and the mixture of the racemic and meso compound was separated by preparative TLC using hexane as the eluent. 1,1-Diphenylethane, butyl propionate (4a), and octyl propionate (4c) were synthesized by hydrogenation of 1,1-diphenylethylene, butyl acrylate (3a), and octyl acrylate (3c) using Pd/C under 1atm H2, respectively. Ethyl 2-phenylacrylate was synthesized by the acid-catalyzed esterification of 2-phenylacrylic acid in ethanol.
30% With vanadium monochloride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;
27% With manganese powder; water monomer In tetrahydrofuran at 20℃; for 24h;
25% With 1-Benzyl-1,4-dihydronicotinamide In pyridine; methanol Irradiation;
10% With methanol for 300h; Irradiation;
94 % Chromat. With lithium triethylhydroborate other reagents, rel. rates;
With hydridotetracarbonylcobalt other alkenes;
With hydridotetracarbonylcobalt In dichloromethane at 0℃;
With tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide 1,1-diarylsubstituted ethenes, electrochemical reduction, var. conc.;
With ethanol; platinum Hydrogenation;
With hydrogenchloride; zinc,6a mercury,6b
With ethanol; nickel Hydrogenation;
With palladium on activated charcoal; ethanol Hydrogenation;
With tetrahydrofuran; palladium(0); cis-cyclohexene
With ethanol; natrium
With ammonia; natrium; toluene Zersetzung des Reaktionsprodukts mit Ammoniumchlorid;
With nickel substance at 230℃; Hydrogenation;
With hydrogen
With hydrogen catalytic hydrogenation;
With hydrogen
With zeolite Ca Y In hexane at 22℃; for 1h;
With dichloromethane; Ca Y zeolite; water monomer 1.) cyclohexane; Yield given. Multistep reaction;
With CaY-500-oven In hexane for 3h; Ambient temperature; Yield given;
With 1% Pd/C; hydrogen
With hydrogen; potasssium hydride In benzene at 60℃; for 18h; Inert atmosphere; Autoclave;
With hydrogen In methanol at 20℃; Darkness;
75 %Chromat. With aluminum terephthalate; ammonia; hydrazine hydrate monohydrate In acetonitrile at 25℃; for 24h; chemoselective reaction;
With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; Butane-1,4-diol; Cs2CO3; bis[2-(diphenylphosphino)phenyl] ether In toluene for 24h; Inert atmosphere; Reflux;
With [{(DIPP-nacnac)CaH(thf)}2]; hydrogen In benzene at 60℃;
Stage #1: 1,1-Diphenylethylene With C18H17Si(1-)*C33H77Ca3N12(1+) In [D8]THF for 3h; Inert atmosphere; Stage #2: With hydrogen In [D8]THF at 60℃; for 312h;
With diethyl ether; tris(pentafluorophenyl)borate; hydrogen at 20℃; for 24h;
92 %Spectr. With hydrogen; bis(pentafluorophenyl)borane In hexadeuterobenzene at 140℃; for 120h;
With hydrogen; tris(2-fluorophenyl)phosphine In dichloromethane-d2 at 20℃;
With hydrogen In isopropanol for 1h; Schlenk technique; Sonication;
Stage #1: 1,1-Diphenylethylene In isopropanol for 0.166667h; Schlenk technique; Sonication; Stage #2: With hydrogen In isopropanol for 0.25h; Schlenk technique;
With hydrazine hydrate monohydrate In ethanol at 80℃; for 18h; Sealed tube; Sonication;
34 %Chromat. With hydrazine hydrate monohydrate In chloroform at 25℃; for 24h;
With [(1,2-bis(diphenylphosphino)ethane)Co(CH2SiMe3)2]; hydrogen In toluene at -196.15 - 25℃; for 5h; Sealed tube;
67 %Spectr. With cyclohexa-1,4-diene; [IPrGaCl2][SbF6] In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;

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[67]Brown, Herbert C.; Kim, Suk-Choong [Journal of Organic Chemistry, 1984, vol. 49, # 6, p. 1064 - 1071]
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[74]Kooyman [Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 117,125]
[75]Braude et al. [Journal of the Chemical Society, 1954, p. 3574,3576]
[76]Klages [Chemische Berichte, 1902, vol. 35, p. 2649][Chemische Berichte, 1906, vol. 39, p. 2591] Klages; Heilmann [Chemische Berichte, 1904, vol. 37, p. 1452]
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[85]Nakamura, Ryota; Obora, Yasushi; Ishii, Yasutaka [Chemical Communications, 2008, # 29, p. 3417 - 3419]
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[89]Maytum, Hannah C.; Francos, Javier; Whatrup, David J.; Williams, Jonathan M. J. [Chemistry - An Asian Journal, 2010, vol. 5, # 3, p. 538 - 542]
[90]Location in patent: scheme or table Zeng, Guixiang; Li, Shuhua [Inorganic Chemistry, 2010, vol. 49, # 7, p. 3361 - 3369]
[91]Jochmann, Phillip; Davin, Julien P.; Spaniol, Thomas P.; Maron, Laurent; Okuda, Jun [Angewandte Chemie - International Edition, 2012, vol. 51, # 18, p. 4452 - 4455]
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[100]Michelet, Bastien; Bour, Christophe; Gandon, Vincent [Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14488 - 14492]
  • 2
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 1483-64-3 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; ammonia; calcium
With diethyl ether; ammonia; barium
With diethyl ether; ammonia; sodium
With diethyl ether; ammonia; sodium anschliessende Behandlung mit NH4Cl;
With diethyl ether; ammonia; barium anschliessende Behandlung mit NH4Cl;
With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide electrochemical reduction; Yield given. Yields of byproduct given;

  • 3
  • [ 612-00-0 ]
  • [ 530-48-3 ]
YieldReaction ConditionsOperation in experiment
With copper chromite; carbon dioxide at 575 - 625℃;
With bromine at 200℃; Gluehlampenlicht;
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide Erwaermen des Reaktionsprodukts mit Pyridin;
80.0 % Chromat. With sulfur dioxide; water at 500℃;
With water at 570℃; for 24h; Gas phase; EXAMPLES; The following examples illustrate the invention without limiting it.; Use is made of a tubular reactor with a diameter of 45 mm which is heated to 570° C. under a pressure of 0.5 bar and which comprises 170 ml of Styromax 3 catalyst. This reactor is fed with DPA and water, which are vaporized beforehand at 310° C., at respective flow rates of 52 and 156 g/h. On exiting from the reactor, after cooling the reaction mixture, ethylbenzene is added at the rate of 13 g/h and separation by settling is carried out at ambient temperature for 15 minutes. An organic phase is obtained which then comprises: DPE: 61.2%; DPA: 11.9%; EB: 19.4%; other products: 6.5%; and water: 500 ppm. After operating for 24 h, 1560 g of DPE are thus recovered and are subsequently treated over a molecular sieve (NK30 from Ceca) to remove the water. This dehydration is carried out by feeding, via the bottom, a column with a length of 1 m and a diameter of 24 mm containing 285 g of molecular sieve. The DPE flow rate is 456 g/h. After percolating through the sieve, the water content of the product is approximately 45 ppm.

  • 4
  • [ 612-00-0 ]
  • [ 103-30-0 ]
  • [ 2779-69-3 ]
YieldReaction ConditionsOperation in experiment
With chlorine at 100 - 150℃; Irradiation;
  • 5
  • [ 612-00-0 ]
  • [ 2186-29-0 ]
YieldReaction ConditionsOperation in experiment
With oxygen
With N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃;
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide; chromium tetra(tert-butoxide) / benzene 2: dihydrogen peroxide; sulfuric acid / diethyl ether / 0 - 5 °C
  • 6
  • [ 612-00-0 ]
  • [ 5670-69-9 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 1,1'-ethylidenebis-benzene With potassium phosphate; barium(II) nitrate; tetrakis(actonitrile)copper(I) hexafluorophosphate; trifluorormethanesulfonic acid; bathophenanthroline In N,N-dimethyl-formamide for 0.0666667h; Inert atmosphere; Stage #2: With ammonium peroxydisulfate; silver trifluoroacetate In N,N-dimethyl-formamide at 110℃; for 22h; Inert atmosphere; Sealed tube; 7 Example 7 First, put a pressure tube with a magnet in an ice water bath, vacuum and fill with nitrogen three times,Add 0.5mL dry DMF and 1mL CF3SO3H in a nitrogen atmosphere and seal,After stirring for 4 minutes, let it stand at room temperature and stir for 4 minutes. then,Add 0.3mmol 1,1-diphenylethane in a nitrogen atmosphere,0.6mmol Ba(NO3)2, 0.015mmol(CH3CN)4CuPF6,Put 0.015mmol 4,7-diphenyl-1,10-phenanthroline, 0.3mmol K3PO4 and 0.5mL dry DMF in a pressure tube, stir for 4 minutes, then add 0.45mmol(NH4)2S2O8,0.06mmol CF3COOAg and 1.0mL dry DMF were stirred for 4 minutes.The reaction mixture is evacuated and filled with inert gas three times and the pressure tube is sealed,Place in an oil bath at 110°C. After reacting for 22 hours, cool to room temperature,Add an appropriate amount of saturated sodium bicarbonate solution to make the reaction liquid neutral, extract three times with ethyl acetate, combine the organic phases, dry with anhydrous magnesium sulfate, filter and concentrate.The concentrate was separated and purified by column chromatography, and the yield of the pure product was 55%.
With nitric acid; acetic acid
With nitric acid; acetic acid
With nitric acid
Multi-step reaction with 2 steps 1: diluted nitric acid 2: acetyl chloride

  • 7
  • [ 612-00-0 ]
  • [ 2319-61-1 ]
YieldReaction ConditionsOperation in experiment
With nickel; methyl cyclohexane at 160 - 200℃; Hydrogenation;
With acetic acid; platinum at 25 - 30℃;
With acetic acid; platinum Hydrogenation;
Multi-step reaction with 2 steps 1: platinum; glacial acetic acid / partielle Hydrierung 2: platinum; glacial acetic acid / Hydrogenation

  • 9
  • [ 599-67-7 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
100% With iodine; hypophosphorous acid In acetic acid at 60℃; for 24h;
99.6% With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 95℃; for 24h; Inert atmosphere;
95% With formic acid; 5%-palladium/activated carbon; ammonium formate In methanol; water at 80℃; for 0.666667h;
94% Stage #1: 1,1-diphenylethanol With n-butyllithium In dichloromethane at 0℃; Stage #2: With dichloroborane In dichloromethane at 0 - 20℃;
92% With chloro-trimethyl-silane; sodium iodide In acetonitrile 0 deg C to 10 deg C then r.t.;
85% With acridine; trifluoroacetic acid In dichloromethane Ambient temperature;
85% With acridine; trifluoroacetic acid In dichloromethane Ambient temperature;
73% With sulfuric acid; hydrogen In ethanol at 25℃; for 20h;
With hydrogen; pyrographite at 300℃;
With hydrogen iodide; acetic acid; zinc
98 % Spectr. With 4,4'-di-tert-butylbiphenyl In tetrahydrofuran for 72h; ultrasonic irradiation;
100 %Spectr. With triethylsilane In dichloromethane for 1h; Reflux; Deoxygenation of benzylic alcohols with Sn-Mont / Et3SiH General procedure: In a round-bottomed flask was placed 30 mg ofSn-Mont, 1 mmol of 1a, 2 mmol of Et3SiH and 5mL of CH2Cl2. The mixture was refluxed for 1 h. Then, Sn-Montwas filtered off, and the filtrate was concentrated and analyzed by NMR usingmesitylene as the internal standard.
87 %Chromat. With hydrogen In ethanol at 80℃; for 5h; Inert atmosphere;
66 %Chromat. With formic acid; methanesulfonic acid; 1,2-bis((di-tert-butylphosphoryl)methyl)benzene; palladium(II) acetylacetonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;

Reference: [1]Gordon, Paul E.; Fry, Albert J. [Tetrahedron Letters, 2001, vol. 42, # 5, p. 831 - 833]
[2]Location in patent: experimental part Milne, Jacqueline E.; Storz, Thomas; Colyer, John T.; Thiel, Oliver R.; Dilmeghani Seran, Mina; Larsen, Robert D.; Murry, Jerry A. [Journal of Organic Chemistry, 2011, vol. 76, # 22, p. 9519 - 9524]
[3]Sawadjoon, Supaporn; Lundstedt, Anna; Samec, Joseph S.M. [ACS Catalysis, 2013, vol. 3, # 4, p. 635 - 642]
[4]Location in patent: scheme or table Yao, Min-Liang; Pippin, Adam B.; Kabalka, George W. [Tetrahedron Letters, 2010, vol. 51, # 5, p. 853 - 855]
[5]Stoner, Eric J.; Cothron, Darlene A.; Balmer, Mary K.; Roden, Brian A. [Tetrahedron, 1995, vol. 51, # 41, p. 11043 - 11062]
[6]Singh, Serjinder; Gill, Sarbjeet; Sharma, Vijay K.; Nagrath, Sarita [Journal of the Chemical Society. Perkin transactions I, 1986, p. 1273 - 1276]
[7]Singh, Serjinder; Gill, Sarbjeet; Sharma, Vijay K.; Nagrath, Sarita [Journal of the Chemical Society. Perkin transactions I, 1986, p. 1273 - 1276]
[8]Gal, Jean-Francois; Maria, Pierre-Charles; Mo, Otilia; Yanez, Manuel; Kuck, Dietmar [Chemistry - A European Journal, 2006, vol. 12, # 29, p. 7676 - 7683]
[9]Zelinsky; Gawerdowskaja [Chemische Berichte, 1928, vol. 61, p. 1052]
[10]Klages; Heilmann [Chemische Berichte, 1904, vol. 37, p. 1452]
[11]Karaman; Kohlman; Fry [Tetrahedron Letters, 1990, vol. 31, # 43, p. 6155 - 6158]
[12]Tandiary, Michael Andreas; Masui, Yoichi; Onaka, Makoto [Tetrahedron Letters, 2014, vol. 55, # 30, p. 4160 - 4162]
[13]Pandarus, Valerica; Ciriminna, Rosaria; Gingras, Geneviève; Béland, François; Pagliaro, Mario; Kaliaguine, Serge [ChemistryOpen, 2018, vol. 7, # 1, p. 80 - 91]
[14]Ciszek, Benjamin; Fleischer, Ivana [Chemistry - A European Journal, 2018, vol. 24, # 47, p. 12259 - 12263]
  • 10
  • [ 3468-99-3 ]
  • [ 612-00-0 ]
  • [ 1883-32-5 ]
YieldReaction ConditionsOperation in experiment
With copper oxide-chromium oxide; hydrogen at 200℃;
  • 12
  • [ 672-65-1 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
64.9% With C9H16N(1+)*Cl(1-)*AlCl3 at 80℃; for 2h; 4.b B, benzene 40g, 1- butyl-3-methylimidazolium chloroaluminate [BMIMCl-AlCl3] 15g, added to the reaction flask, a solution of 2-chloro-2-phenylethane at 80 45g, 2 drops Xiaoshi after further reaction for 2 hours, cooled to room temperature, the reaction mixture was allowed to stand stratification, the upper organic phase was separated, the organic phase was washed with water and caustic to neutral, distillation recovery of excess benzene to give 1,1-diphenylethane the crude product was collected by distillation 127 / 8mmHg product was obtained 1,1-diphenylethane.
63% With magnesium oxide at 50℃; for 8h;
With aluminium trichloride
  • 13
  • [ 74-86-2 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
  • [ 22566-43-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; mercury(II) sulfate at 10 - 20℃;
  • 14
  • [ 100-42-5 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
78% With gold(III) chloride; silver hexafluoroantimonate In benzene at 50℃; for 5h; Inert atmosphere; Darkness;
With aluminium trichloride
With aluminium trichloride at 40℃;
With sulfuric acid at 30 - 35℃;
With phosphotungstic acid supported on mesoporous silica nanosphere at 70℃; for 5h;

  • 15
  • [ 75-34-3 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
64.6% With 1-butyl-3-methylimidazolium-aluminum trichloride [BMIMBr-AlCl3] ionic liquid catalyst at 50℃; for 5h; 4 Example 4 Benzene 65 g,Ionic liquid catalyst1-butyl-3-methylimidazolium bromide, -Aluminum trichloride [BMIMBr-AlCl3]Add reaction bottle,50 under uniform speed to the reaction system25 g of 1,1-dichloroethane was added dropwise,In 3.5 hours drop finished,Continue for 1.5 hours.After completion of the reaction,First, the temperature of the reaction system was lowered to room temperature,Then, the reaction solution was allowed to stand still,Separating the upper organic phase,The organic phase was washed with water,Alkaline wash to neutral,Then excess benzene is recovered by distillation,To give 1,1-diphenylethane crude product,The product of 126-129 [deg.] C / 8 mm Hg was collected by rectification,To give 1,1-diphenylethane.
With aluminium trichloride
With aluminium trichloride at 70℃;
  • 16
  • [ 75-01-4 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride
With aluminium trichloride at 0 - 5℃;
  • 17
  • [ 13323-81-4 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
61% With cerium(III) sulfate at 125 - 130℃;
With aluminium trichloride
  • 18
  • [ 67-56-1 ]
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 1483-64-3 ]
  • [ 1883-32-5 ]
  • [ 20017-67-8 ]
  • [ 39153-68-9 ]
  • [ 74421-26-4 ]
  • 19
  • [ 67-56-1 ]
  • [ 5216-46-6 ]
  • [ 530-48-3 ]
  • [ 4541-89-3 ]
  • [ 612-00-0 ]
  • [ 1483-64-3 ]
  • [ 20017-67-8 ]
  • [ 41976-80-1 ]
  • 20
  • [ 67-56-1 ]
  • [ 947-40-0 ]
  • [ 612-00-0 ]
  • [ 1883-32-5 ]
  • [ 20017-67-8 ]
  • [ 4801-14-3 ]
  • [ 74421-26-4 ]
  • 21
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 612-00-0 ]
  • [ 4279-81-6 ]
  • [ 20017-67-8 ]
  • 22
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 10496-82-9 ]
YieldReaction ConditionsOperation in experiment
1: 90% 2: 5% With titanium(III) citrate; Tris buffer; tetra(n-butyl)ammonium hydroxide In ethanol
With hydrogen In acetone at -78℃; for 0.5h;
  • 23
  • [ 108-86-1 ]
  • [ 74-85-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
65% With tetrabutylammomium bromide; water; lithium perchlorate; nickel dibromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 0 - 5℃; The reaction was carried out by electrolysis.;
  • 24
  • [ 119-61-9 ]
  • [ 917-54-4 ]
  • [ 530-48-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
1: 90% 2: 90% With <<(n-PrO)3WCl2>2> In tetrahydrofuran -78 deg C -> RT, 1 h, then reflux, 3 h;
  • 25
  • [ 591-50-4 ]
  • [ 74-85-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
60% With tetrabutylammomium bromide; water; lithium perchlorate; nickel dibromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 0 - 5℃; The reaction was carried out by electrolysis.;
  • 26
  • [ 612-00-0 ]
  • [ 103057-10-9 ]
  • 4-(2,2-Diphenyl-propyl)-1-trityl-1H-imidazole [ No CAS ]
  • 27
  • [ 612-00-0 ]
  • [ 599-67-7 ]
YieldReaction ConditionsOperation in experiment
With methyltrifluoromethyldioxirane In acetone at 0℃;
With potassium hydroxide; potassium permanganate In dichloromethane; water Ambient temperature; Yield given;
Stage #1: 1,1'-ethylidenebis-benzene With triethylsilane; oxygen In acetonitrile for 1h; Irradiation; Stage #2: With triphenylphosphine
With dihydrogen peroxide; C28H38F3MnN4O7S(1+)*CF3O3S(1-); acetic acid In acetonitrile at 0℃; for 3h;

  • 28
  • [ 612-00-0 ]
  • [ 10605-46-6 ]
YieldReaction ConditionsOperation in experiment
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 39 percent / aq. HNO3 / Ambient temperature 2: 1.) N-bromosuccinimide, benzoyl peroxide, 2.) pyridine / 1.) CCl4, irradiation, reflux, 165 min, 2.) reflux, 75 min
Multi-step reaction with 2 steps 1: HNO3 2: dibenzoyl peroxide; CCl4; <i>N</i>-bromo-succinimide / Erhitzen des Reaktionsprodukts mit Pyridin
  • 29
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  • [ 612-00-0 ]
  • [ 947-40-0 ]
YieldReaction ConditionsOperation in experiment
1: 88% 2: 43% With acetyl chloride In dichloromethane 1.) 0 deg C, 2.) room temperature, 1 h; Yield given;
  • 30
  • [ 544-97-8 ]
  • [ 90-99-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
95% With titanium tetrachloride In dichloromethane at 0℃; for 2h;
  • 31
  • [ 20017-67-8 ]
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 4279-81-6 ]
  • 32
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 612-00-0 ]
  • [ 4279-81-6 ]
  • [ 22875-82-7 ]
YieldReaction ConditionsOperation in experiment
With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In benzene at 120℃; for 48h; Yield given. Yields of byproduct given;
  • 33
  • N-(p-toluenesulfonyl)-DL-alanine [ No CAS ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
74% With sulfuric acid at 60 - 70℃;
  • 34
  • [ 5558-67-8 ]
  • [ 612-00-0 ]
  • [ 34611-07-9 ]
YieldReaction ConditionsOperation in experiment
1: 52% 2: 27% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 24h;
  • 35
  • [ 285120-11-8 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
42% With methanol at 40 - 50℃; for 96h;
  • 36
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 612-00-0 ]
  • [ 4279-81-6 ]
YieldReaction ConditionsOperation in experiment
1: 69% 2: 5% With hydrogen In water; toluene at 100℃; for 48h;
  • 37
  • [ 50373-55-2 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
62 % Chromat. With dihydrogen hexachloroplatinate at 140℃; for 20h;
50 % Chromat. With iron(III) chloride at 140℃; for 20h;
21 %Chromat. With 1-butyl-3-methylimidazolium tetrachloridoferrate(III) at 80℃; for 12h; regioselective reaction;
  • 38
  • [ 612-00-0 ]
  • [ 119-61-9 ]
  • [ 2186-29-0 ]
YieldReaction ConditionsOperation in experiment
With triethylsilane; oxygen In acetonitrile at 5 - 10℃; for 0.5h; Irradiation;
  • 39
  • [ 67-56-1 ]
  • [ 789-02-6 ]
  • [ 612-00-0 ]
  • [ 2387-16-8 ]
  • [ 3469-00-9 ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 22% 3: 16% With hydrogen; triethylamine at 20℃; for 24h;
  • 40
  • [ 50-29-3 ]
  • [ 612-00-0 ]
  • [ 72-54-8 ]
  • [ 3547-04-4 ]
  • [ 60617-89-2 ]
YieldReaction ConditionsOperation in experiment
1: 30% 2: 29% 3: 12% 4: 15% 5: 8% 6: 6% With hydrogen; triethylamine In methanol at 20℃; for 0.5h;
  • 41
  • [ 50-29-3 ]
  • [ 612-00-0 ]
  • [ 2387-16-8 ]
YieldReaction ConditionsOperation in experiment
1: 69% 2: 31% With hydrogen; triethylamine In methanol at 20℃; for 4h;
  • 42
  • [ 72-55-9 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen; triethylamine In methanol at 20℃; for 0.5h;
> 99 %Chromat. With Pd(0)/HAP; hydrogen; caesium carbonate In isopropyl alcohol at 60℃; for 1h;
  • 43
  • [ 72-55-9 ]
  • [ 612-00-0 ]
  • [ 3547-04-4 ]
  • [ 60617-89-2 ]
YieldReaction ConditionsOperation in experiment
1: 33% 2: 23% 3: 44% With hydrogen; triethylamine In methanol at 20℃; for 0.166667h;
  • 44
  • [ 72-54-8 ]
  • [ 612-00-0 ]
  • [ 2387-16-8 ]
YieldReaction ConditionsOperation in experiment
1: 27% 2: 73% With hydrogen; triethylamine In methanol at 20℃; for 24h;
  • 45
  • [ 140-10-3 ]
  • [ 71-43-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
79% With H-ZSM5 zeolite at 130℃; for 20h;
  • 46
  • [ 60702-29-6 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
98% With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;
97% With tetraazaethylene-type neutral organic super-electron donor In N,N-dimethyl-formamide at 110℃; for 18h;
97% Stage #1: (1-(phenylsulfonyl)ethane-1,1-diyl)dibenzene With C3H6C9H10N4 In N,N-dimethyl-formamide at 110℃; Inert atmosphere; Stage #2: In water Inert atmosphere;
70% With C24H32N8Ni(2+)*2I(1-); sodium amalgam In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
15% With 4-(dimethylamino)-1-methylpyridinium-2-carboxylate In N,N-dimethyl-formamide at 150℃; for 24h; Schlenk technique; Inert atmosphere;

  • 47
  • [ 50-29-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
87% With Pd(0)/HAP; hydrogen; caesium carbonate In isopropyl alcohol at 60℃; for 28h;
Multi-step reaction with 2 steps 1: 12 percent / H2; Et3N / Pd/C / methanol / 0.5 h / 20 °C 2: 27 percent / H2; Et3N / Pd/C / methanol / 24 h / 20 °C
Multi-step reaction with 2 steps 1: 34 percent / H2; Et3N / Pd/C / methanol / 0.17 h / 20 °C 2: 27 percent / H2; Et3N / Pd/C / methanol / 24 h / 20 °C
With tetramethylammonium tetrafluoroborate In water-d2; N,N-dimethyl-formamide Electrolysis;
Multi-step reaction with 2 steps 1: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide / Electrolysis 2: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide; water-d2 / Electrolysis
Multi-step reaction with 2 steps 1: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide / Electrolysis 2: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide; water-d2 / Electrolysis
Multi-step reaction with 2 steps 1: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide / Electrolysis 2: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide; water-d2 / Electrolysis
Multi-step reaction with 2 steps 1: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide / Electrolysis 2: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide; water-d2 / Electrolysis
Multi-step reaction with 3 steps 1: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide / Electrolysis 2: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide / Electrolysis 3: tetramethylammonium tetrafluoroborate / N,N-dimethyl-formamide; water-d2 / Electrolysis

  • 48
  • [ 612-00-0 ]
  • [ 100869-80-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 39 percent / aq. HNO3 / Ambient temperature 2: 1.) N-bromosuccinimide, benzoyl peroxide, 2.) pyridine / 1.) CCl4, irradiation, reflux, 165 min, 2.) reflux, 75 min 3: 96 percent / SnCl2*2H2O / ethanol / 0.5 h / 70 °C
  • 49
  • [ 612-00-0 ]
  • [ 144791-88-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 39 percent / aq. HNO3 / Ambient temperature 2: 1.) N-bromosuccinimide, benzoyl peroxide, 2.) pyridine / 1.) CCl4, irradiation, reflux, 165 min, 2.) reflux, 75 min 3: 96 percent / SnCl2*2H2O / ethanol / 0.5 h / 70 °C 4: 1.) aq. HCl, NaNO2, 2.) NaN3 / 1.) 0 deg C to 5 deg C, 1.5 h, 2.) 15 min
  • 50
  • [ 100-44-7 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
54.4% III EXAMPLE III EXAMPLE III The procedure of Example I was repeated except that benzyl chloride was added in 3 portions (10.7 g, 8.0g, and 7.3 g) at 1.75 hr intervals and the total reaction time was only 6 hr at 85° C. The yield of diphenylethane was 9.9 g, i.e. a 54.4% yield.
  • 51
  • [ 7439-89-6 ]
  • [ 100-44-7 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
In methanol; water I EXAMPLE I EXAMPLE I A 250 ml, three necked, round-bottom flask was equipped with a mechanical stirrer, a reflux condenser, a thermometer, and an addition funnel. The flask was charged with water (120ml) and hydrogen-reduced 97% pure iron powder (5.5g, 0.1 mol). (The iron powder was obtained from Aldrich Chemical Company, Inc, and was stated to contain copper and Cu(I) salts.) The flask contents were heated and stirred under nitrogen to a temperature of 95° C. Benzyl chloride (25.3g, 0.2 mol) was then added in 2 min. The reaction mixture was stirred at 85° C. under nitrogen for 23 hr. The heating was discontinued and stirring was stopped. The contents were cooled with ice. The solid top layer formed after cooling was separated from the reaction mass by filtration. The solids contained iron which was removed by dissolving the alkanol-soluble solids in 100 ml of methanol. The iron was not soluble in the methanol and was removed therefrom by filtration. The remaining methanol solution was evaporated to yield pale yellow crystals weighing 11.4 g (62.6% yield). The melting point of the crystals was 48° C.-52° C. (Aldrich, pure diphenylethane mp is 50° C.).
  • 52
  • [ 612-00-0 ]
  • [ 106-48-9 ]
  • [ 71643-17-9 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In benzene 11 2-(5-chloro-2-hydroxybenzyl)-6-[1-(3,5-dichloro-2-hydroxyphenyl)ethyl]-4-fluorophenol (36) p-Chlorophenol (2.5 g) was heated to 60° and a trace of p-toluenesulphonic acid added. The 1,1-diphenylethane obtained above (1.5 g) was added slowly to the melt. After the addition was complete, benzene (50 ml) was added and the solution was heated under reflux for 14 hrs to remove water from the reaction mixture. The product was purified by column chromatography to give 2-(5-chloro-2-hydroxy-benzyl)-6-[1-(3,5-dichloro-2-hydroxyphenyl) ethyl]-4-fluorophenol (1.1 g m.p. 166°). Compounds No 35, 45 and 47 of Table I were prepared by an analogous process to that described above for the preparation of compound no 36.
  • 53
  • [ 612-00-0 ]
  • [ 13007-92-6 ]
  • C6H5CH(C6H5)CH3Cr(CO)3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% In not given boiling;;
23% In not given boiling;;
  • 54
  • [ 100-42-5 ]
  • [ 4406-72-8 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
91% With potassium <i>tert</i>-butylate; oxygen; (-)-sparteine In isopropyl alcohol at 55℃; for 24h;
91% With potassium <i>tert</i>-butylate; oxygen; isopropyl alcohol at 55℃; for 24h; 4.2 Diaryl methane units are prevalent in biologically active small molecules and this method can allow the rapid highly regioselective synthesis of this functionality. To explore the scope of the reductive coupling of boronic esters and styrenes, the above conditions were used to synthesize a variety of diaryl methane-containing products (Table 6). All of the reductive coupling reactions are highly regioselective (>25:1), and the reactions of simple coupling partners give high yields (78-91%) of isolated diaryl methane-containing products (Table 6, entries 1-3). The results demonstrate that substrates containing acid-sensitive functional groups are stable to the reductive coupling reaction conditions; for example, acetal protecting groups, which are readily removed upon work up, are compatible with the reaction conditions (Table 6, entries 5-7). Arylboronic esters containing electron-donating groups react more slowly, thereby requiring a higher catalyst loading (Table 6, entries 8 and 9), and ortho substitution on the arylboronic acid is tolerated (Table 6, entry 10). The ester functionality is also compatible, however an increase in [sp] is required to achieve a 63% yield of 3k (Table 6, entry 11). On the basis of our previous mechanistic hypothesis that the formation of a ϖ-benzyl intermediate is responsible for the outstanding regioselectivity, a diene substrate, which can form a similar ϖ-allyl species, was evaluated and yielded the reductive coupling product 31 in 41% yield as a greater than 25:1 mixture of regioisomers (Table 6, entry 12). Under these conditions both vinylboronic esters and simple alkenes, which rapidly isomerize, do not undergo an effective reductive coupling reaction. Even though a chiral additive (sp) is used, less than 5% enantiomer excess (ee) is observed for the product.After exploring the scope, there were three mechanistic questions to address: 1) what is the efficiency of alcohol oxidation as compared to product formation? 2) why are three equivalents of the arylboronic ester required for good product yields? and 3) why is exogenous sp required for catalysis? To investigate the first question, a higher molecular weight alcohol, sec-BuOH, was used as the solvent in order to use GC analysis to effectively measure the amount of ketone being formed via alcohol oxidation. A time course analysis of the reaction was performed and the GC yields of the hydroarylation product 3a and butan-2-one (5) as well as the percent styrene 1a remaining were plotted as a function of time (FIG. 4a). Initially, the yield of 3a and 5 are equivalent until 60% conversion, which is consistent with the oxidation of one alcohol directly yielding product. This also suggests that the PdII-hydride formed via alcohol oxidation reacts with the alkene faster than it reductively eliminates. In contrast, as the reaction progresses to higher substrate conversion, the yield of the 5 increases at a rate different than that of product formation. This shows as the concentration of alkene decreases, the PdII-hydride can undergo other competitive reactions including reductive elimination. The GC yield of 3a was 78% in sec-BuOH as compared to 91% in IPA indicating a modest solvent dependence.The next question investigated was, why are three equivalents of 2a required? Therefore, the fate of the boronic ester was investigated as the reaction progressed (FIG. 4b). Over an equivalent of 2a was consumed at 30 minutes after which a relatively linear decrease in concentration was observed (the scatter can be attributed to hydrolysis of 2a on silica before GC analysis). Besides the hydroarylation product 3a, two major byproducts, biphenyl (6) and phenol (7), derived from the boronic ester were observed. A 10% GC yield of biphenyl, the product of oxidative boronic acid homocoupling, is formed at 2 h, but a 14% yield of biphenyl (0.28 equiv. of 2a consumed) is observed overall. Phenol is the major byproduct of this reaction and is formed consistently throughout the reaction (1.3 equiv. of 2a). Phenol is likely formed from the reaction of the boronic ester with H2O2 formed from the reduction of O2 during catalyst regeneration. Together these data account for the undesired pathways that consume the excess arylboronic ester required.The final mechanistic question was the role(s) of sp considering that performing the reaction without exogenous sp leads to poor catalysis. Several functions of sp can be envisioned including acting as a ligand to stabilize Pd0 during catalyst regeneration, acting as a ligand on PdII during the reductive coupling process, and/or to break up the dimeric [Pd(SiPr)Cl2]2 complex. The first two roles are difficult to directly probe, however an experiment was performed to investigate the feasibility of sp breaking up the dimer complex. The experiment involved dissolving [Pd(SiPr)Cl2]2 and 2 equiv. of sp in 1,2-dichloroethane (DCE). The resulting mixture was heated to reflux for 2 h (FIG. 5). An aliquot of the mixture was analyzed by ESI-MS. Excitingly, the major Pd-complex observed in solution corresponds to Pd(SiPr)(sp)Cl2 [m/z (MH+)+=801.3]. Based upon the trans-geometry of related Pd(NHC)(pyridine)Cl2 complexes, the formation of complex 8 in which the NHC ligand is trans to the monodendate sp ligand is a proposed mechanism. Unfortunately, attempts to isolate complex 8 only led to the [Pd(SiPr)Cl2]2 complex and free sp. This shows that complex 8 is in equilibrium with the dimer. It should be noted that Pd[(-)-sparteine]Cl2 is not observed by ESI-MS. Interestingly, other simple amine bases do not lead to an effective catalytic system for reductive coupling. Possible explanations for this are the large size of sp facilitates ligand dissociation or the free nitrogen of sp could act as an intramolecular base.
91% With di-μ-chlorobis[chloro(N,N'-bis-(2,6-(diisopropyl)phenyl)imidazolidine-2-ylidene)palladium]; potassium <i>tert</i>-butylate; oxygen; isopropyl alcohol; (-)-sparteine at 55℃; for 24h; regioselective reaction;
  • 55
  • [ 87245-79-2 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
With (SiR)-1-isopropyl-(1,2,3,4-tetrahydro)-1-silanaphthalene; triphenylborane In toluene at 20℃; for 2h; Inert atmosphere;
  • 56
  • [ 856374-18-0 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 2,2-diphenylethyl 4-methylbenzoate With samarium diiodide In Norlaudanosolin Inert atmosphere; Reflux; Stage #2: With water; ammonium chloride In Norlaudanosolin Inert atmosphere;
  • 57
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 104217-70-1 ]
YieldReaction ConditionsOperation in experiment
With (2-dimethylamino-α-trimethylsilylbenzyl)2Ca*(THF)2; hydrogen In tetrahydrofuran at 20℃; for 3.5h; Inert atmosphere; Autoclave;
  • 58
  • C47H62CaN2O [ No CAS ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In benzene at 20℃; for 15h; Inert atmosphere; Autoclave;
  • 59
  • [ 68602-47-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In tetrahydrofuran at 20℃; for 17h; Inert atmosphere; Autoclave;
  • 60
  • [ 5433-78-3 ]
  • [ 75-24-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane; toluene at 25℃; for 2h; Inert atmosphere;
  • 61
  • [ 38661-81-3 ]
  • [ 100-58-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
96% With dichloro bis(acetonitrile) palladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;
  • 62
  • [ 72-54-8 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
> 99 %Chromat. With Pd(0)/HAP; hydrogen; caesium carbonate In isopropyl alcohol at 60℃; for 1h;
  • 63
  • [ 108-86-1 ]
  • [ 1524-12-5 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #3: 1-phenylethyl 2,2,2-trifluoroacetate With zinc(II) chloride In toluene at 50℃; for 24h; Inert atmosphere;
  • 65
  • [ 87057-91-8 ]
  • [ 75-24-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
92% In n-heptane; dichloromethane at 20℃; for 1h;
  • 66
  • [ 1450-14-2 ]
  • [ 599-67-7 ]
  • [ 612-00-0 ]
  • [ 53173-01-6 ]
YieldReaction ConditionsOperation in experiment
With 1% Au/TiO2 In ethyl acetate at 55℃; for 2h; Overall yield = 94 %;
  • 67
  • [ 4545-21-5 ]
  • [ 4426-21-5 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In 1,4-dioxane at 110℃; for 2h; Inert atmosphere; Reflux;
  • 68
  • [ 110-89-4 ]
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 2591-86-8 ]
  • [ 612-00-0 ]
  • [ 4279-81-6 ]
  • [ 3540-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 13.1%Chromat. 2: 10.6%Chromat. 3: 10.2%Chromat. 4: 47% With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; C64H38F16P4; hydrogen In toluene at 125℃; for 60h; Autoclave;
1: 44.1%Chromat. 2: 23.5%Chromat. 3: 11.8 %Chromat. 4: 7% With (biphenyl-2,2’,6,6’-tetramethanediyl)tetrakis(diphenylphosphane); bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen In toluene at 125℃; for 60h; Autoclave;
  • 69
  • [ 110-89-4 ]
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 612-00-0 ]
  • [ 4279-81-6 ]
  • [ 3540-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 11.7%Chromat. 2: 6.7%Chromat. 3: 81% With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,1'-Binaphthalin-2,2'-diylbis(methylen)bis(diphenylphosphan); hydrogen In toluene at 125℃; for 60h; Autoclave;
1: 40.2%Chromat. 2: 22.4%Chromat. 3: 29% With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 125℃; for 60h; Autoclave;
  • 70
  • [ 110-89-4 ]
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 2591-86-8 ]
  • [ 612-00-0 ]
  • [ 3540-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 13.8%Chromat. 2: 5.6%Chromat. 3: 85% With [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; 1,1'-Binaphthalin-2,2'-diylbis(methylen)bis(diphenylphosphan); hydrogen In toluene at 125℃; for 60h; Autoclave;
1: 40%Chromat. 2: 22.1%Chromat. 3: 48% With [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; 1,1'-Binaphthalin-2,2'-diylbis(methylen)bis(diphenylphosphan); hydrogen In methanol at 125℃; for 60h; Autoclave;
  • 71
  • [ 110-89-4 ]
  • [ 530-48-3 ]
  • [ 201230-82-2 ]
  • [ 612-00-0 ]
  • [ 3540-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 34.7 %Chromat. 2: 23% With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; triphenylphosphine In toluene at 125℃; for 60h; Autoclave;
  • 72
  • [ 1016-09-7 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
99% With palladium dichloride In methanol at 40℃; for 12h; Inert atmosphere; Green chemistry; chemoselective reaction;
  • 73
  • [ 2058-74-4 ]
  • [ 60702-29-6 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 1-methyl-1H-indole-2,3-dione With sodium amalgam In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: (1-(phenylsulfonyl)ethane-1,1-diyl)dibenzene In N,N-dimethyl-formamide at 110℃; for 18h;
  • 74
  • [ 591-50-4 ]
  • [ 174090-36-9 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
66% With styrene; tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate; triphenylphosphine; silver(l) oxide In 1,2-dimethoxyethane at 85℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;
  • 75
  • [ 100-42-5 ]
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 100-41-4 ]
YieldReaction ConditionsOperation in experiment
1: 95% 2: 18% With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen at 20℃; for 3h;
  • 76
  • [ 1078-58-6 ]
  • [ 38661-81-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 at 20℃; for 0.166667h; Inert atmosphere; Glovebox;
  • 77
  • [ 5558-66-7 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
91% With methanol at 40℃; for 24h; Schlenk technique; Irradiation; Inert atmosphere;
83% With 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; diphenyldisulfane In 2,2,2-trifluoroethanol at 20℃; for 24h; Glovebox; Irradiation; Sealed tube;
  • 78
  • [ 5558-67-8 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride; lithium iodide In tetrahydrofuran; mineral oil at 85℃; for 7h; Inert atmosphere; Sealed tube;
  • 79
  • [ 4279-81-6 ]
  • [ 530-48-3 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
1: 78% 2: 6% With 5 mol% Pd/C In cyclohexane at 130℃; for 24h; Inert atmosphere; Molecular sieve; Sealed tube; Decarbonylation of 3-phenylpropanal to ethylbenzene (2a) [CAS Reg. No. 100-41-4] General procedure: Dry glass reaction tube purged with argon and equipped with a magnetic stir bar was chargedwith molecular sieves (3-4 Å, 100 mg), aldehyde 1a (50 μL, 0.38 mmol), Pd/C (20 mg, 5 mol%Pd), and cyclohexane (1 mL) and the sealed tube was heated at 130 °C for 24 h. The reaction mixture was cooled to room temperature, filtered through a pad of Celite, and washed withCH2Cl2 (15 - 20 mL). Compound 2a was obtained, GC-MS yield: 67%, based on naphthalene asa standard.
1: 71% 2: 9% With palladium 10% on activated carbon; oxygen; sodium carbonate In isopropyl alcohol at 120℃; for 24h; regioselective reaction;
  • 80
  • [ 108-86-1 ]
  • [ 672-65-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
92% With nickel(II) iodide; potassium fluoride; 4,4'-dimethyl-2,2'-bipyridines; zinc In N,N-dimethyl acetamide at 25℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique; Method A; General Procedure General procedure: To a flame-dried Schlenk tube equipped with a stir bar was loaded aryl bromide (0.3 mmol, 100 mol%) and benzyl chloride (0.6 mmol, 200 mol%), followed by addition of ligand 1b (0.03 mmol, 10 mol%), zinc powder (39 mg, 0.6 mmol, 300 mol%), and MgCl2 (28.6 mg, 0.3 mmol, 100 mol%). The tube was moved into an anhydrous glove box, then NiI2 (9.4 mg, 0.03 mmol, 10 mol%) was added. The tube was capped with a rubber septum and moved out of the glove box. N,N-Dimethylacetamide (1 mL) and pyridine (24 μL, 0.3 mmol, 100 mol%) were added by using a syringe. The mixture was stirred for 16 h under N2 atmosphere at 25 °C, then directly loaded onto a silica column without work-up. The residue in the reaction vessel was rinsed with small amount of petroleum ether. Flash column chromatography provided the product as a solid or oil.
  • 81
  • [ 4545-21-5 ]
  • [ 98-80-6 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,4-dioxane at 110℃; for 5h; General procedure for the one-pot, two-step reactions of acetyl naphthalenederivatives, TsNHNH2, with arylboronic acids General procedure: A solution of the acetyl naphthalene derivatives (0.5 mmol) and tosylhydrazide (0.75 mmol) in 3mL of toluene/dioxane was stirred at 80 °C for 2 h in a reaction tube. Potassium carbonate (1.5mmol) and the appropriate arylboronic acids (0.75 mmol) were added to the reaction mixture. The system was refluxed at 110 °C for 5 h with stirring. When the reaction was complete, the crude mixture was allowed to reach room temperature. Dichloromethane and a saturated solution of NaHCO3 were added and the layers were separated. The aqueous phase was extracted three times with dichloromethane. The combined organic layers were washed with two portions of a saturated solution of NaHCO3, one portion of brine and then dried over MgSO4 and filtered. The solvent was removed under reduced pressure. The products were purified by chromatography on silica gel.
  • 82
  • [ 100-41-4 ]
  • [ 15961-35-0 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
60% With 1,10-Phenanthroline; copper(I) iodide dimethyl sulfide complex; di-tert-butyl peroxide In chlorobenzene at 90℃; for 48h; Inert atmosphere; Glovebox; Sealed tube;
  • 83
  • [ 599-67-7 ]
  • [ 612-00-0 ]
  • [ 19303-32-3 ]
YieldReaction ConditionsOperation in experiment
1: 46 %Spectr. 2: 53 %Spectr. With hydrogen iodide In neat (no solvent) at 25℃; Inert atmosphere; 3.3. Procedure for the reaction of benzyl alcohols with HI gas General procedure: In a round bottom ask tted with three-way cock with septumwas placed benzyl alcohol analogue (1.0e1.5 mmol). The ask waslled with nitrogen after reducing pressure. After slight decom-pression to ease to the gas introduction, HI gas (0.5e2.0 equiv.) wasbrought in the vessel with syringe through the septum (the weightof HI gas was calculated the change of the weight of the equipmentbefore and after the introduction of HI gas). And nitrogen gas wasintroduced into vessel to release deference of pressure against at-mosphere. The mixture stood at 25C for 2 d. After reducingpressure to release HI gas, to the reaction mixture was addedsaturated Na2S2O3 (20 mL) and brine (15 mL). After being extractedwith CHCl3 or Et2O (15 mL 3), the organic layer was dried withMgSO4. After the concentration, ca. 10.0 mg of the residue wascombined with p-chlorobenzaldehyde (ca. 10.0 mg) as an internalstandard. And the mixture was measured with1H NMR to deter-mine the yield by the integration of methyl, methylene or methinepeak of the product and formyl peak of p-chlorobenzaldehyde(9.98 ppm). Furthermore, the reaction mixture included in p-chlorobenzaldehyde was subject to column chromatography onSiO2 to give the product.Iodinated products, (iodomethyl)benzene (2a),29(1-iodoethyl)benzene (2b),30and reduction products, diphenylmethane (3d),311,1-diphenylethane (3e),32triphenylmethane (3f),33wereassigned by the corresponding proton peaks at benzylic positionscompared with the chemical shift reported in the literature.
  • 84
  • [ 108-86-1 ]
  • [ 103-63-9 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
90% With nickel(II) bromide dimethoxyethane; Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]2(1,10-phenantroline)PF6; Bathocuproine; diisopropylamine; magnesium bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; regioselective reaction;
85% With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;
  • 85
  • [ 100-42-5 ]
  • [ 98-80-6 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
73% With methanol; bis(1,5-cyclooctadiene)nickel (0); tri-tert-butyl phosphine In toluene at 60℃; for 1h; Inert atmosphere; Glovebox; regioselective reaction;
  • 86
  • [ 100865-93-8 ]
  • [ 75-24-1 ]
  • [ 612-00-0 ]
  • [ 100865-92-7 ]
YieldReaction ConditionsOperation in experiment
1: 91% 2: 8% With aluminum (III) chloride In dichloromethane at 20℃; for 0.5h;
  • 87
  • [ 100865-93-8 ]
  • [ 75-24-1 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: trimethylaluminum With aluminum (III) chloride In hexane; dichloromethane for 0.0833333h; Inert atmosphere; Stage #2: O-diphenylmethyl 2,2,2-trichloroacetimidate In hexane; dichloromethane at 0 - 20℃; for 0.25h; Inert atmosphere;
  • 88
  • [ 24388-23-6 ]
  • [ 672-65-1 ]
  • [ 612-00-0 ]
  • 2,3-diphenylbutane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2-bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)acetonitrile; (2,2-bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)acetonitrile)FeCl; lithium ethylmethyl amide In benzene at 20℃; for 24.25h; Inert atmosphere; Sealed tube;
  • 89
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 632-50-8 ]
YieldReaction ConditionsOperation in experiment
With C142H196Ba2N4; hydrogen In benzene-d6 at 30℃; for 8h; Autoclave; Glovebox; Schlenk technique;
  • 90
  • 1,1-diphenylethyl formate [ No CAS ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
89% With triethylsilane; C19H3BF14 In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;
  • 91
  • [ 530-48-3 ]
  • [ 14315-12-9 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
1: 82 %Spectr. 2: 13 %Spectr. With iodine; sulfur In toluene at 130℃; for 4h; Inert atmosphere; Schlenk technique; Procedures for the iodine-mediated sulfuration reaction of 1,1-diarylethylenes 6 General procedure: General procedure: A 30 mL two-neck pear shaped flask charged with 6 (1 equiv) and S8 (4 equiv) was equipped with a septum, a magnetic stirring bar, and a cold finger which was placed on one port of a vacuum manifold. After the atmosphere was replaced with nitrogen gas, the vacuum manifold line was switched to a balloon of nitrogen gas. Then, I2 (Conditions A: 1 equiv, Conditions B: 4 equiv) and toluene (3.03 mL/mmol) were added to the flask at room temperature. The resulting flask was immersed in an oil bath maintained at 130 °C (Conditions A: for 4 h, Conditions B: for 24 h). After cooling to room temperature, the mixture was quenched with sat. Na2S2O3 aq. and extracted with Et2O (three times). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The yield was determined by 1H NMR analysis of the crude mixture using 1,4-bis(trimethylsilyl)benzene as the internal standard.
  • 92
  • [ 530-48-3 ]
  • [ 14315-12-9 ]
  • [ 612-00-0 ]
  • [ 206-75-7 ]
YieldReaction ConditionsOperation in experiment
1: 52 %Spectr. 2: 36 %Spectr. 3: 6 %Spectr. With iodine; sulfur In toluene at 130℃; for 24h; Inert atmosphere; Schlenk technique; Procedures for the iodine-mediated sulfuration reaction of 1,1-diarylethylenes 6 General procedure: General procedure: A 30 mL two-neck pear shaped flask charged with 6 (1 equiv) and S8 (4 equiv) was equipped with a septum, a magnetic stirring bar, and a cold finger which was placed on one port of a vacuum manifold. After the atmosphere was replaced with nitrogen gas, the vacuum manifold line was switched to a balloon of nitrogen gas. Then, I2 (Conditions A: 1 equiv, Conditions B: 4 equiv) and toluene (3.03 mL/mmol) were added to the flask at room temperature. The resulting flask was immersed in an oil bath maintained at 130 °C (Conditions A: for 4 h, Conditions B: for 24 h). After cooling to room temperature, the mixture was quenched with sat. Na2S2O3 aq. and extracted with Et2O (three times). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The yield was determined by 1H NMR analysis of the crude mixture using 1,4-bis(trimethylsilyl)benzene as the internal standard.
  • 93
  • [ 119-61-9 ]
  • [ 917-54-4 ]
  • [ 612-00-0 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: benzophenone; methyllithium In tetrahydrofuran at -50 - 0℃; for 2h; Inert atmosphere; Stage #2: With hexylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;
  • 94
  • [ 100-59-4 ]
  • [ 622-24-2 ]
  • [ 100-42-5 ]
  • [ 612-00-0 ]
  • [ 100-41-4 ]
  • [ 103-29-7 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; [(1,1′-bis(diphenylphosphino)ferrocene)Ni(0)(1,5-cyclooctadiene)] In tetrahydrofuran at 85℃; for 24h;
  • 95
  • [ 100-59-4 ]
  • [ 103-63-9 ]
  • [ 100-42-5 ]
  • [ 612-00-0 ]
  • [ 100-41-4 ]
  • [ 103-29-7 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; [(1,1′-bis(diphenylphosphino)ferrocene)Ni(0)(1,5-cyclooctadiene)] In tetrahydrofuran at 85℃; for 24h;
  • 96
  • [ 17376-04-4 ]
  • [ 100-59-4 ]
  • [ 100-42-5 ]
  • [ 612-00-0 ]
  • [ 100-41-4 ]
  • [ 103-29-7 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1′-bis(diphenylphosphino)ferrocene)Ni(I)Cl In tetrahydrofuran at 85℃; for 24h;
  • 97
  • [ 612-00-0 ]
  • [ 90155-46-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trisaminocyclopropenium; water; N,N,N,N-tetraethylammonium tetrafluoroborate; trifluoroacetic acid / Electrochemical reaction; Irradiation 2: potassium hydroxide; ethanol / ethylene glycol / Reflux
  • 98
  • [ 612-00-0 ]
  • [ 112717-66-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trisaminocyclopropenium; water; N,N,N,N-tetraethylammonium tetrafluoroborate; trifluoroacetic acid / Electrochemical reaction; Irradiation 2: potassium hydroxide; ethanol / ethylene glycol / Reflux 3: methanol / 20 °C
  • 99
  • [ 612-00-0 ]
  • [ 75-05-8 ]
  • C18H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With trisaminocyclopropenium; water; N,N,N,N-tetraethylammonium tetrafluoroborate; trifluoroacetic acid Electrochemical reaction; Irradiation;
  • 100
  • [ 612-00-0 ]
  • [ 119-61-9 ]
  • [ 93-99-2 ]
YieldReaction ConditionsOperation in experiment
1: 88% 2: 10% With 2,2'-azobis(isobutyronitrile); oxygen; nickel dibromide In chloroform at 75℃; for 48h; AIBN/O2 initiated oxidation of diphenylethanes General procedure: A solution of 1a (0.5 mmol), NiBr2 (15 mol %) and AIBN (2.0 mmol) in CHCl3 (10 mL) was stirred at 75 oC under O2 atmosphere. After completion monitored by TLC (by UV visualization), the solvent was removed under reduced pressure. The products were separated by silica gel column chromatography eluted with petroleum ether/ ethyl acetate (v/v 30:1) to afford the product in pure form. Benzophenone (2a) [1] Following the procedure 1 (24 h) and 2 (48 h), 2a was isolated in 82% and 88% yields, respectively. 1H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 7.1 Hz, 4H), 7.55 (t, J = 7.4 Hz, 2H), 7.45 (t, J = 7.8 Hz, 4H); 13C NMR (101 MHz, CDCl3) δ 196.7, 137.6, 132.4, 130.0, 128.3.
1: 20% 2: 44% With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; for 72h;
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