Lewis/Bronsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans

作者:Chen, Zan; Huang, Wenting; Su, Yu; Jiang, Huanfeng; Wu, Wanqing*
来源:Chemical Communications, 2023, 59(30): 4523-4526.
DOI:10.1039/d3cc00787a

摘要

A novel Lewis- and Bronsted-acid mediated electrophilic addition cyclization/amidation reaction of 1,6-enynes with nitriles to synthesize 3-enamide-substituted dihydrobenzofurans has been developed. The transformation involves the addition of a Bronsted acid as the electrophilic reagent to enynes, followed by intramolecular cyclization to form cationic intermediates, and the termination of the reaction by a nitrile as a nucleophile. The main features of the reaction include high atom economy and chemoselectivity, as well as the construction of C-C/C-N bonds in one step.

全文