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

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,Ndimethylacetamide. 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.

Automated summary

A copper-based system enables the methylene insertion reaction between an amine and a milder nucleophile, such as a terminal alkyne, through the cleavage of the C-N bond in N,N-dimethylacetamide. This method provides a convenient access to propargylic amines with good to excellent yields. The wide substrate scope and the ability to functionalize complex molecules at late stages make this protocol practically valuable.