Palladium-catalyzed chemoselective N-monoallylation of aromatic amines with diallylamine through a borrowing hydrogen strategy

Abstract

A palladium-catalyzed N-monoallylation reaction of aromatic amines with diallylamine at relatively low temperatures has been established for the synthesis of N-monoallylated amines via a borrowing hydrogen strategy. Employing diallylamine as the allylating agent, primary (hetero)aryl amines, N-alkyl secondary (hetero)aryl amines, N,N-diarylamines, and various commercially available aniline-containing pharmaceuticals can be utilized to synthesize N-monoallyl aromatic amines with releasing ammonia as the by-product.