Catalytic Methylene Insertion between Amines and Terminal Alkynes via C–N Bond Cleavage of N,N-Dimethylacetamide: A Unique Route to Propargylic Amines

• DOI: 10.1021/acs.joc.2c02584
• Publication Date: 2023-01-17T01:03:46Z
• Authors: Ajijur Rahaman; Rupali Dasharath ...; Sukalyan Bhadra
• Keywords: 01 natural sciences; 0104 chemical sciences

A copper-based system allows for the methylene insertion between an amine and a milder nucleophile, including a terminal alkyne counterpart, via C-N bond cleavage of N,N-dimethylacetamide. The method gives an expedient access to propargylic amines in good to excellent yields. A wide-ranging substrate scope and late-stage functionalization of complex molecules make the protocol practically valuable.