Palladium-catalysed vinylation of organic halides with terminal alkenes

Abstract

There are relatively few basic type reactions that generate a new carbon-carbon bond, although this is one of the most critical operations in the synthesis of organic molecules. Vinylic derivatives are versatile compounds in the synthetic chemistry and hence a method for their synthesis has been explored. In view of the extensive natural occurrence and biological importance of unsaturated ester a general method for the synthesis of substituted acrylate through palladium-catalyzed reaction using arylhalide and alkyl acrylate is reported. R=CH3 R=CzHs R=n-C4H9 CH=CHCOOR X=H X=p-CH30 X=p-CH3 X = o-NHCOCH3 X=p-Cl X=p-NOz X=p-COOH X 18-28 (PPh3h PdCIz, DMF • CHz=CH-COOR Et3N, rt, 30 hrs 8-14 I X The coupling reaction was carried out by stirring a mixture of aryliodide 8-14 and alkylacrylate 15-17 in presence of bis (triphenylphosphene) palladium (II) chloride as a catalyst and triethylamine as a base in dimethylformamide (DMF) at room temperature. The condensed product was purified by column chromatography to afford unsaturated ester 18-28. The ester was subjected to hydrolysis to yield unsaturated carboxylic acid 29-31. The synthesized compounds were characterized based on analytical data obtained from IR, UV, IHNMR 13CNMR and melting points.