| 99% |
With potassium carbonate In water at 20℃; for 1h; |
|
| 98% |
With Triphenylmethylamin; potassium carbonate; palladium dichloride In water at 20℃; for 16h; |
|
| 97% |
With potassium carbonate In ethanol; water at 60℃; for 3h; |
|
| 96% |
With trans-{PdCl2-[η1-(P)-PPh2(p-C6H4NMe2)]2}; potassium carbonate In water; isopropyl alcohol at 20℃; for 24h; |
|
| 96% |
With potassium carbonate In ethanol at 78℃; for 1h; Air atmosphere; |
|
| 96% |
With C26H26N4O8Pd2; potassium carbonate In water at 20℃; for 24h; |
General procedure for the Suzuki-Miyaura reaction
General procedure: A 50 ml round bottom flask was charged with a mixture of aryl halide (0.5 mmol), arylboronic acid (0.55 mmol), K2CO3 (1.5 mmol), and Pd catalyst (0.2 mol% for aryl bromide or 1 mol% for aryl chloride) and the mixture was stirred for required times at room temperature in water (6 ml) for aryl bromides/at 80 °C in aqueous-glycerol (6 ml) for aryl chlorides. After completion, the reaction mixture was diluted with water (20 ml) and extracted with ether (20 ml × 3). The combined extract was washed with brine (20 ml × 3) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, ethyl acetate/hexane 1:9) to obtain the desired product. The products were confirmed by comparing the 1H NMR and mass spectral data with authentic samples. |
| 96% |
With potassium carbonate In water; isopropyl alcohol at 28℃; for 4h; |
5.5 Standard Procedure for Suzuki-Miyaura Reaction
General procedure: A 50 ml round-bottom flask was charged with a mixture of aryl halide (0.5 mmol), arylboronic acid (0.55 mmol), K2CO3 (1 mmol), catalyst (10 mg, 0.22 mol% Pd) and i-PrOH/H2O (4 mL). The mixture was stirred at room temperature for the indicated time. After completion, the reaction mixture was subjected to centrifugation followed by filtration and the residual solid was washed with the same solvent (3 X 5 mL). The resultant filtrate was diluted with brine (10 mL) and extracted with diethyl ether (3 9 mL), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The crude residue was subjected to silica gel column chromatography (ethyl acetate-hexane, 0.5: 9.5) to obtain the desired products. |
| 95% |
With C21H15ClN2O2Pd; potassium carbonate In water at 50℃; for 0.416667h; |
General procedure for Suzuki Miyaura reaction
General procedure: A 25 mL synthesizer tube was taken with a mixture of aryl halide (0.5 mmol), aryl boronic acid (0.55 mmol),base (1.5 mmol), Pd-complex C1 (0.2 mol %) and the mixture was stirred in2 mL of water at 50°C for the required time. After completion, the reaction mixture was extracted with ether (3 Χ 20 mL). The combined extract was washed with brine (2 Χ 20 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel,ethyl acetate-hexane: 1:9) to obtain the desired products. The products were confirmed by comparing the 1H and 13C NMR and mass spectral data with authentic samples. |
| 95% |
With 1-phenylethanone-O-(4-chloro-phenyl)oxime; tetrabutylammomium bromide; potassium carbonate; palladium dichloride In water at 27℃; for 4.5h; Green chemistry; |
Typical experimental procedure for Suzuki-Miyaura reaction of aryl bromideswith aryl boronic acids
General procedure: All the reactions were carried out in open atmosphere. A mixture of arylbromide (0.5 mmol), aryl boronic acid (0.55 mmol), K2CO3 (1 mmol), PdCl2(1 mol %), ligand (2 mol %), TBAB (0.5 mmol), and water (4 mL) was stirred atroom temperature for the indicated time in a 25 mL round bottom flask. Theprogress of the reaction was monitored using TLC (Merck silica gel 60F254plates) under UV light. After completion, the reaction mixture was diluted withbrine (10 mL) and extracted with ether (3 10 mL). The combined extract wasdried over anhydrous Na2SO4. After evaporation of ether under vacuum, theproduct was isolated by short-chromatography {silica gel (60-120 mesh), ethylacetate-hexane; 0.5:9.5}. The isolated products were confirmed by comparingtheir 1H and 13C NMR and mass spectral data with reported samples |
| 95% |
With C21H20N2O2Pd; potassium carbonate In water; isopropyl alcohol at 25℃; for 1h; |
General procedure for Suzuki Miyaura reaction
General procedure: A 25 mL synthesiser tube had taken with a mixture of aryl halide (0.5 mmol), aryl boronic acid (0.55 mmol), base (1.5 mmol), Pd complex C1 (0.2 mol %) and the mixture was stirred in 2 mL of aqueous isoproponol (1:1) at room temperature for the required time. After completion, the reaction mixture was extracted with ether (3 × 20 mL). The combined extract was washed with brine (2 × 20 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, ethyl acetate-hexane: 1:9) to obtain the desired products.The products were confirmed by comparing the 1H and 13C NMR and mass spectral data with authentic samples. |
| 95% |
With potassium carbonate In water; isopropyl alcohol at 28℃; for 8h; |
|
| 95% |
With potassium carbonate In water; isopropyl alcohol at 28℃; for 8h; |
|
| 95% |
With water extract of waste papaya bark ash; palladium diacetate In ethanol at 28℃; for 0.333333h; Green chemistry; |
|
| 95% |
With dichloro bis(acetonitrile) palladium(II); C95H120N20O10(10+)*10F6P(1-); potassium carbonate In ethanol at 50℃; for 1.5h; |
General procedure for the Suzuki coupling reactions
General procedure: In a typical run, a mixture of aryl bromide (0.50 mmol),phenylboronic acid (0.55 mmol), K2CO3 (1.5 mmol),0.2 mol% ligand, 1 mol% PdCl2(CH3CN)2 in 1.5 mL of ethanol were stirred at 50 C for 1.5 h under air. Solvent ethanol was removed completely under vacuum degree0.09 MPa at 45 C to give a crude product. The pure product was isolated by column chromatography on silica. |
| 94% |
With potassium carbonate In ethanol; water at 80℃; for 5h; Inert atmosphere; |
|
| 93% |
With potassium carbonate In ethanol; water at 78℃; for 0.5h; Green chemistry; |
|
| 93% |
With [2,6-(iPr)2C6H3-N=C(Ph)-C(Ph)(Me)-OH]PdCl2; sodium carbonate In ethanol; water at 60℃; for 2h; |
2.3 General procedure for Suzuki-Miyaura reaction
General procedure: In a round bottle, palladium complexes (0.01 mol% mmol), aryl halides (1.0 mmol), arylboronic acid (1.2 mmol), base (2.0 mmol) and 4 ml of solvent were added with a magnetic stir bar. The reaction mixture was carried out at the described temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 ml), followed by extraction twice (2 × 5 ml) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20/1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR. |
| 93% |
With potassium carbonate In water at 75℃; for 5h; |
General experimental procedure for Suzuki reaction
General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 °C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product. |
| 93% |
With C34H28Cl2N2P2Pd(2+); potassium carbonate In water; isopropyl alcohol at 20℃; for 3h; |
|
| 91% |
With potassium carbonate In ethanol; water at 20℃; Green chemistry; |
|
| 91% |
With C56H44N2OP2Pd(2+)*2ClO4(1-); potassium carbonate In water at 20℃; for 20h; |
|
| 90% |
With C22H26N2O6Pd2; potassium carbonate In isopropyl alcohol at 20℃; for 18h; |
|
| 90% |
With potassium carbonate In water at 90℃; for 0.833333h; |
2.3 General Procedure for Suzuki Coupling Reaction
General procedure: Mixture of iodobenzene (0.5 mmol), boronic acid(0.75 mmol), K2CO3 (1.25 mmol), PdNP-PG catalyst(0.1 mol %), and water as a solvent (2 mL) was stirred at 90 °C for appropriate time as indicated in Table 1 entry 5.The progress of the reaction was monitored by TLC. The reaction mass was cooled after completion of the reaction and the catalyst was separated by filtration. The product was extracted from aqueous layer by using 10 mL ethylacetate. The combined organic layer was dried on anhydrous sodium sulphate, concentrated under reduced pressure and was purified by column chromatography on silicagel (Hexane/EtOAc: 98:2) to get the product. |
| 89% |
With N,N,N',N'-tetramethyl-N'',N''-didodecyl-guanidinium bromide; water; palladium diacetate; potassium carbonate In ethanol at 70℃; for 5h; |
|
| 89% |
With palladium diacetate In water; isopropyl alcohol at 27℃; for 1.5h; |
General experimental procedure for Suzuki-Miyaura reaction:
General procedure: A 50 mL round-bottom flask was charged with a mixture of arylboronic acid (1.2 mmol), aryl halide (1 mmol), 2 mL distilled water and 2 mL of iso-propanol. To this mixture, 1 mol% of Pd(OAc)2 was added followed by the addition of the 0.3 g of rice straw ash. The whole reaction mixture was stirred for the required time resulting a black colored solution. The reaction was monitored by TLC and after completion of the reaction, the solution was extracted with ethylacetate (3x10 mL). The products were purified by column chromatography and finally confirmed by 1H and13C NMR spectroscopy. |
| 88% |
With 3,5-di-tert-butyl-2-hydroxybenzaldehyde; potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 2h; |
General procedure for Suzuki-Miyaura reaction
General procedure: To a round bottle with a magnetic stir bar, ligand (0.01% mmol), PdCl2 (0.01% mmol), aryl halides (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol) and 6 ml of solvent were added. The reaction mixture was conducted at room temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 mL), followed by extraction twice (2×5 mL) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The conversions rates were analyzed by gas chromatography, based on the peak area normalization method. The corrected factor was determined by samples against a standard of n-heptane. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20:1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR. |
| 86% |
|
1 4-(4-Chlorophenyl)-nitrobenzene
4-(4-Chlorophenyl)-nitrobenzene Was prepared according to method C from 4-bromonitrobenzene and 4-Chlorophenyl boronic acid. Yield 86%. Mp 141.6-145.2° C. |
| 86.8% |
With potassium carbonate In ethanol at 80℃; for 6h; Green chemistry; |
|
| 82% |
With potassium carbonate In ethanol; water for 4h; Reflux; In air; |
|
| 82% |
With potassium carbonate In ethanol; water at 20℃; for 3h; |
|
| 73% |
With sodium carbonate In tetrahydrofuran at 60℃; for 3h; |
|
| 71% |
With sodium carbonate In tetrahydrofuran; water at 60℃; for 5h; |
|
| 52% |
With Triphenylmethylamin; potassium carbonate; palladium dichloride In water for 0.0333333h; Microwave irradiation; |
|
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