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Radical Monofluoroalkylative Alkynylation of Olefins by a Docking–Migration Strategy
Author(s) -
Wang Min,
Zhang Huihui,
Liu Jige,
Wu Xinxin,
Zhu Chen
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910514
Subject(s) - alkynylation , alkene , chemistry , docking (animal) , combinatorial chemistry , radical , substrate (aquarium) , stereochemistry , organic chemistry , catalysis , medicine , nursing , geology , oceanography
A radical‐mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking–migration sequence, affording a vast array of valuable fluoroalkyl‐substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late‐stage alkynylation.