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‐α,β‐disubstituted amides ( gem or E1; 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 α,β‐unsaturated amides was also successfully achieved. Traces of products were observed in the absence of p ‐toluenesulfonic acid used as an additive. The reaction is sensitive to the type of phosphine ligand and solvent. Copyright © 2002 John Wiley & Sons, Ltd.