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Alkene Difunctionalization Triggered by a Stabilized Allenyl Radical: Concomitant Installation of Two Unsaturated C−C Bonds
Author(s) -
Wei Yunlong,
Zhang Hong,
Wu Xinxin,
Zhu Chen
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106145
Subject(s) - alkene , radical , chemistry , degree of unsaturation , intermolecular force , combinatorial chemistry , photochemistry , aryl , reagent , medicinal chemistry , alkyl , organic chemistry , molecule , catalysis
Radical‐mediated difunctionalization of alkenes provides a promising approach to introduce one alkenyl or alkynyl group to target compounds. However, simultaneous installation of two unsaturated C−C bonds via alkene difunctionalization remains elusive, attributable to the high instability and transient lifetimes of alkenyl and alkynyl radicals. Herein, we report the photocatalytic 1,2‐alkynylalkenylation and 1,2‐enynylalkenylation of alkenes for the first time, triggered by the intermolecular addition of a stabilized allenyl radical to an alkene. A portfolio of strategically designed, easily accessible dual‐function reagents are applied to a radical docking‐migration cascade. The protocol has broad substrate scope and efficiently increases the degree of unsaturation.