Ni-catalyzed regio- and diastereoselective syn-alkynylamination of unactivated alkenes using alkylamine sources†

Abstract

The three-component alkynylamination of alkenes is a prevalent and powerful platform for rapid access to homopropargyl amines. However, the use of alkylamines to achieve this transformation remains a significant challenge. Here, we report a nickel-catalyzed intermolecular selective alkynylamination of unactivated alkenes to access the corresponding homopropargyl amines as single diastereomers. This protocol offers a range of alkylamine sources, including secondary and primary alkyl amines, as well as even the less sterically hindered primary amines, and demonstrates high functional group compatibility with alkynylsilanes. Additionally, the reaction can be applied to late-stage modifications of natural products and drugs, resulting in good yields and excellent diastereoselectivities.