One-carbon homologation of aryl and alkyl aldehydes to amides using BtCH2P+Ph3Cl-

Abstract

One-carbon homologated amides have been prepared from aryl and alkyl aldehydes. Vinyl benzotriazoles 6, prepared by the reaction of aldehydes with the one-carbon synthon BtCH2P+Ph3Cl- (5), weresubsequently brominated to give 1,2-dibromo-benzotriazolylalkanes 7. Treatment of 7 with a variety of aryl or alkyl amines in the presence of water furnished one-carbon homologated amides 8a-r in 32-95% yields. This method works well with both primary and secondary aryl or alkyl amines.