Palladium(II) acetate catalyzed efficient synthesis of N-aryl-α,β-unsaturated amides via carbonylative addition of aniline derivatives to aromatic alkynes

A series of new N-aryl-alpha,beta-disubstituted amides (gem or El; trans or E2) were synthesized in good yields by carbonylative addition of aniline derivatives 1a-f to aromatic alkynes 2a,b catalyzed by Pd(OAc)(2) and 1,3-bis (diphenylphosphino) propane. The catalytic synthesis of tertiary alpha,beta-unsaturated amides was also successfully achieved. Traces of products were observed in the absence of p-toluenesuffortic acid used as an additive. The reaction is sensitive to the type of phosphine ligand and solvent. Copyright (C) 2002 John Wiley Sons, Ltd.