Metal-free direct amidation of alkynes using N-Boc-O-tosyl-hydroxylamine via Cope-type hydroamination and Beckmann rearrangement

Abstract

The conversion of alkynes into amides has largely relied on transition-metal catalysis, whereas metal-free approaches remain scarcely explored. Herein, we report a metal-free, direct amidation of alkynes using N-Boc-O-tosylhydroxylamine (TsONHBoc) in the presence of water and catalytic triflic acid. This transformation proceeds via Cope-type hydroamination, followed by Beckmann rearrangement, providing efficient access to a wide range of amides.