| 96% |
With air In N,N-dimethyl-formamide at 20℃; for 16h; Green chemistry; |
|
| 95% |
With Tetradecanoic acid 1-methylethyl ester; palladium diacetate; potassium carbonate In water monomer at 20℃; for 0.25h; Green chemistry; |
|
| 94% |
With air In methanol at 20℃; |
|
| 93% |
With palladium diacetate; triphenylphosphine at 70℃; for 8h; |
|
| 93% |
With copper(II) dichloride dihydrate; anhydrous sodium carbonate In methanol at 25℃; for 0.25h; Green chemistry; |
2. General procedure for homocoupling reactions of arylboronic acids
General procedure: Arylboronic acid (0.3 mmol), CuCl2·2H2O (2.5 mg, 5 mol%), Na2CO3 (10 mol%),methanol (1 mL) were added to a vial. The reaction mixture was stirred at 25 °C inthe air for 5-15 min and was monitored by TLC. Then the reaction was quenched withtwo drops of H2O, diluted with 2 mL of ethyl acetate, and filtered over a pad ofMgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solutionwas concentrated in vacuum. The crude material was loaded onto a silica gel columnand purified by flash chromatography. |
| 91% |
With CpPd(SIPr)Cl; potassium-t-butoxide In isopropanol at 25℃; for 24h; Inert atmosphere; |
|
| 90% |
With Cu<SUB>2</SUB>(ophen)<SUB>2</SUB> In N,N-dimethyl-formamide at 20℃; for 20h; |
4.3. Catalytic tests: general procedure I for the Cu2(ophen)2catalyzed homocoupling for Table 2
General procedure: 4.3. Catalytic tests: general procedure I for the Cu2(ophen)2catalyzed homocoupling for Table 2 A solution of the corresponding arylboronic acids (1.0 mmol),Cu2(ophen)2 (1.3 mg, 0.5 mol %), DMF (1.0 mL) in 5 mL round-bottomed ask was stirred under air and the reaction was moni-tored by TLC. After the substrate was consumed, the reaction con-versions were determined bygas chromatography (GC) analysis (FIDfrom AGILENT 7820) using a cross-linked (95%)-dimethyl-(5%)-diphenylpolysil-oxane column (HP-5, 30 m0.32 mm0.25 mm),helium, injector temperature 250 C, detector temperature 300 C,and oven temperature program 45 C (3 min)e20C/mine280 C(2 min). The resulting mixture was poured into brine (10 mL), andextracted with diethyl ether (310 mL). The organic layer waswashed with brine, dried over Mg2SO4, the residue was chromato-graphed via a short column of silica gel (petroleum ether: diethylether15:1) and evaporated under reduced pressure. The productswas determined by 1H NMR spectroscopy. All 1H NMR spectra weremeasured in CDCl3 with TMS as the internal standard. |
| 90% |
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 5h; |
General procedure for homocoupling of arylboronicacid
General procedure: In a 50 mL round bottomed flask phenylboronic acid (1mmol), DMF (2 ml), catalyst (60 mg), KOH (1 mmol) wereadded and this heterogeneous mixture was vigorously stirredfor the required time at room temperature. After completionof reaction (monitored by TLC), the reaction mixture was filteredto separate the catalyst. The organic product was extractedwith ethyl acetate (3x10 ml). The combined organicfractions were dried over sodium sulphate and concentrated.The residue was purified by silica gel column chromatographywith hexane as eluent to afford the desired product. Theprepared products were characterized by NMR and massspectral analysis. |
| 90% |
With palladium diacetate at 20℃; for 0.333333h; |
|
| 89% |
With oxygen; potassium carbonate In water monomer at 25℃; for 2h; Green chemistry; |
Representative procedure for the nano CuO catalyzed homocoupling of arylboronic acid
General procedure: A solution of nano CuO (0.010 mmol) and substituted phenylboronic acid (1 mmol) in H2O (2 mL) was stirred at 25 °C for 2 h under aerobic condition. After the reaction was over, the reaction mixture was extracted with ethyl acetate and washed with doubledistilled water in a separating funnel. The organic layer was separated and collected in a conical flask. After evaporation of the solvent in a rotary evaporator, reaction mixture was subjected to column chromatography on silica gel column (ethyl acetate/hexane, 1:10) to afford the respective product. |
| 88% |
With palladium(II) complex of ferrocene appended N-heterocyclic carbene supported on silica; air In water monomer at 20℃; for 10h; |
2.4 General Procedure for Synthesis of Biaryls
General procedure: A suspension of aryl boronic acid (5) (0.5mmol, 0.0610g) and SilFemBenzNHCPd complex (4) (50mg) in water(5mL) was stirred at room temperature. After completion of the reaction as monitored by thin layer chromatography(TLC), the insoluble complex was filtered and washed with copious amount of water. The filtrate was extracted withethyl acetate (3 × 5mL). The combined extracts were driedover Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography over silicagel to give pure biaryls which were characterized by FT-IR,1H-NMR, 13C-NMR and mass spectroscopy. |
| 86% |
With sodium chlorine monoxide; tetrabutylammonium bromide; palladium (II) chloride In water monomer at 70℃; |
|
| 86% |
With tripotassium phosphate tribasic In 1,4-dioxane at 85℃; for 3h; Green chemistry; |
|
| 85% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium diacetate; tetraethylammonium perchlorate; potassium carbonate In water monomer; acetonitrile at 20℃; Electrochemical reaction; Divided cell; Inert atmosphere; |
|
| 85% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium diacetate; tetraethylammonium perchlorate; potassium carbonate In water monomer; acetonitrile at 20℃; Inert atmosphere; Electrochemical reaction; |
|
| 85% |
With Cs2CO3; cobalt(II) chloride In N,N-dimethyl acetamide at 20℃; Irradiation; |
3 General procedure for the preparation of biaryls from arylboronic acids:
General procedure: The above-mentioned ligand (0.6 mmol), metal salt (0.5 mmol), and solvent (10 mL) were added to the reaction flask, stirred at room temperature for 1 hour, then arylboronic acid (10 mmol) and base (12 mmol) were added to connect with oxygen or air, And irradiate blue light or white light, after the reaction, extract with water and ethyl acetate three times, collect the organic phase, dry with anhydrous sodium sulfate, remove the solvent with a rotary evaporator, and then purify it by silica gel chromatography to obtain pure biaryl compounds . |
| 84% |
With p-benzoquinone In methanol at 20℃; for 24h; |
|
| 84% |
With potassium carbonate In water monomer at 60℃; for 0.0833333h; Microwave irradiation; Green chemistry; |
|
| 83% |
With [Cu(1-(9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl)-1H-1,2,4-triazole)2(H2O)(N,N-dimethylformamide)](NO3)2*3H2O; Cs2CO3 In N,N-dimethyl-formamide at 20℃; for 24h; |
|
| 82% |
With chlorotris(triphenylphosphine) rhodium (I); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In 1,4-dioxane; water monomer at 130℃; for 2h; Inert atmosphere; |
|
| 80% |
With [Pd(Phbz)(OAc)(PPh3)] In tetrahydrofuran at 20℃; for 24h; Schlenk technique; |
|
| 79% |
With sodium tetrachloridoaurate(III) dihydrate; potassium carbonate In ethanol at 50℃; for 24h; |
Representative experimental procedure: A mixture of AuCl (11.6 mg, 0.050 mmol), phenylboronic acid (1a, 121.9 mg, 1.00 mmol), K2CO3 (152.0 mg, 1.10 mmol) in EtOH (8.0 mL) was heated at 50 °C under open air for 24 h. The reaction mixture was filtered through a plug of Florisil washing with hexane-AcOEt (3:1). The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to preparative thin-layer chromatography (hexane:AcOEt = 20:1) to afford biphenyl (2a, 58.6 mg, 76%). |
| 72% |
With oxygen; Cs2CO3 In ethanol; water monomer at 20℃; for 4h; Green chemistry; |
|
| 71% |
With air; [{(1,10-phenanthroline)Cu(μ-OH)}2Cl2]*3H2O In isopropanol at 28℃; for 2h; |
|
| 60% |
With C30H24N2O2Pd; anhydrous sodium carbonate In toluene for 6h; Reflux; |
|
| 56% |
With copper (I) iodide; (E)-2-((2-(pyridin-2-yl)hydrazono)methyl)pyridine; cobalt(II) chloride hexahydrate; potassium carbonate In acetonitrile at 20℃; for 8h; Irradiation; |
|
| 98 %Chromat. |
With [Cu2Br2(bis[3,5-dimethyl-4-(4'-pyridyl)pyrazol-1-yl]methane)]n*nH2O} In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; |
|
|
Multi-step reaction with 2 steps
1: iodine; potassium carbonate / toluene / 7 h / 70 °C / 750.08 Torr / Inert atmosphere
2: iodine; potassium carbonate / toluene / 7 h / 70 °C / 750.08 Torr / Inert atmosphere |
|
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
