Metal-free synthesis of nitriles from aldehydes using N-Boc-O-tosylhydroxylamine as a nitrogen source

Abstract

Herein, we have demonstrated an economical and practical approach to nitriles from readily available aldehydes using stable N-Boc-O-tosylhydroxylamine (TsONHBoc) as the aminating agent. This direct transition metal-free method tolerates a wide range of functional groups and provides aromatic, aliphatic, heteroarylic and α,β-unsaturated nitriles in excellent yields. Bench-stability, ease of handling and in situ generation of a highly reactive N-source under mild and benign reaction conditions add additional advantages for a potential scale-up synthesis.