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With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; under 750.075 Torr; for 2h;Autoclave;
General procedure: Catalytic reactions were carried out in a Teflon-linedstainless steel autoclave (50 mL) equipped with a magneticstirrer bar and an automatic temperature controller. In atypical experiment, 0.5 mol% Pd, aryl iodide (1.0 mmol),amine (3.0 mmol) and K2CO3 (414.6 mg, 3.0 mmol) wereadded to DMF (4 mL) and allowed to react under COatmosphere (1 bar) at 120 C for 2-4 h. After the reaction,the reactor was cooled to room temperature. The reactionmixture was centrifuged at 5000 rpm for 10 min, and theclear supernatant, to which was added ethyl phenylacetateas an internal standard, was analyzed with GC. For the studyof substrate scope, after completion of the reaction, thecatalyst was centrifuged at 5000 rpm for 10 min and theclear supernatant was diluted with 20 % HCl and extractedwith diethyl ether. The organic layer was washed withsaturated NaHCO3 and NaCl solutions, respectively, driedover anhydrous Na2SO4 and evaporated under vacuum afterfiltration. The residue obtained was purified by columnchromatography (silica gel, 200-300 meshes; petroleum-ethyl acetate, 20:1) to afford the pure products. All productswere confirmed by 1H and 13C NMR analyses. For therecycling experiment, the solid catalyst was separated bycentrifugation from the reaction mixture, washed threetimes with the reaction solvent (DMF) and then engaged ina new catalytic cycle under the same reaction conditions.All the synthesized amides are known products, and wehave reported recently [28].
84%
With triethylamine; In N,N-dimethyl acetamide; at 130℃; under 15001.5 Torr; for 1.5h;Autoclave; Green chemistry;
General procedure: reactionThe catalytic reactions were carried out in a 150 ml stainlesssteel autoclave equipped with a mechanical stirrer. Palladium cat-alyst (0.07 mmol), aryl iodide (10 mmol), amine (20 mmol), base(30 mmol) and solvent (15 ml) were loaded into the reactor. Theautoclave was purged three times with CO and pressurized to1.5 MPa with CO at room temperature. The reaction was carriedout at 130C for appropriate time. After the reaction, the reactorwas cooled to room temperature and depressurized. The reac-tion mixture was centrifuged at 5000 rpm for 10 min and the clearsupernatant which was added naphthalene as an internal standardwas analyzed with GC. For the study of substrate scope, after com-pletion of the reaction, the catalyst was centrifuged at 5000 rpmfor 10 min and the clear supernatant was diluted with 20% HCland extracted with diethyl ether. The organic layer was washedwith saturated NaHCO3and NaCl solutions, respectively, dried overanhydrous Na2SO4, and evaporated under vacuum after filtration.The residue obtained was purified by column chromatography (sil-ica gel, 200-300 mesh; petroleum-ethyl acetate, 20:1) to afford thepure products.
With Wilkinson?s catalyst; 1,3-bis-(diphenylphosphino)propane; water; In tetrahydrofuran; at 140℃; for 12h;Inert atmosphere; Sealed tube;
General procedure: Rh(PPh3)3Cl (2.5 mol%) and DPPP (0.04 mmol) were transferred into an oven-dried tube(15 mL), which was evacuated and backfilled with N2 (5x). THF(2 mL), H2O (1 mmol), aryl iodides (1.2 mmol), furfural (1 mmol)and amine (1.8 mmol) were added into the tube via syringe and sealed with Teflon plug. The reaction mixture was stirred at 140 C for 12 h. After the reaction was complete, the mixture was concentrated by rotary evaporation. The crude product was purified by column chromatography (EA/PE = 1/20) on a silica gel to afford the desired product.
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