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With copper(l) iodide; sodium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 120℃; for 16h;Inert atmosphere;
General procedure: 5-Aryl oxazole 2 (0.69 mmol) and 4-iodobenzene/4-iodobenzoic acid (0.83 mmol) were taken in dry DMF (10 mL). Copper iodide (0.69 mmol) and triphenyl phosphine (0.2mmol) were then added sequentially. To this mixture sodiumc arbonate (1.39 mmol) in little excess was added at one portion and the resulting mixture was stirred at 120 C for 16 h under inert atmosphere (N2). The whole mixture was concentrated by removing excess DMF using vacuum pump and then it was diluted with dichloromethane (30 mL). The entire organic solution was sequentially washed with water (15 mL × 3), 3 % HCl (15 mL) and half saturated brine solution (20 mL). Finally the organic layer was dried over anhydrous sodium sulphate. It was then concentrated in vacuo and was purified by column chromatography using petroleum ether-ethyl acetate (3:1) as eluent to get the product as colourless solid. The formation of the product was further confirmed by spectroscopic data.
With bis(1,5-cyclooctadiene)nickel(0); caesium carbonate; 1,2-bis-(dicyclohexylphosphino)ethane; In para-xylene; at 140℃; for 21h;Glovebox; Sealed tube;
General procedure: Ni(COD)2, ligand (dcype or dcypt), base (Cs2CO3 or K3PO4), and azole were weighed into in an oven dried 20 mL scintillation vial in the glove box. A xylene solution of the aryl electrophile (pivalates, mesylates or carbamates) was added to the reaction mixture. The reaction vial was sealed with a Teflon lined cap, taken out of the glove box and the reaction mixture was allowed to stir at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.0 inch plug of silica gel, eluting with Et2O (125 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product.
With bis(1,5-cyclooctadiene)nickel(0); 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); caesium carbonate; In para-xylene; at 140℃; for 22h;Glovebox; Sealed tube;
General procedure: Ni(COD)2, ligand (dcype or dcypt), base (Cs2CO3 or K3PO4), aryl electrophile (pivalates, mesylates or carbamates) and azole were weighed into in an oven dried 20 mL scintillation vial in the glove box. Xylene was added, the vial was sealed with a Teflon lined cap, taken out of the glove box and the reaction mixture was allowed to stir at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.0 inch plug of silica gel, eluting with Et2O (125 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product.
With bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); In para-xylene; at 140℃; for 22h;Glovebox; Sealed tube;
General procedure: Ni(COD)2, ligand (dcype or dcypt), base (Cs2CO3 or K3PO4), and azole were weighed into in an oven dried 20 mL scintillation vial in the glove box. A xylene solution of the aryl electrophile (pivalates, mesylates or carbamates) was added to the reaction mixture. The reaction vial was sealed with a Teflon lined cap, taken out of the glove box and the reaction mixture was allowed to stir at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.0 inch plug of silica gel, eluting with Et2O (125 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product.
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