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Regioselective Vinylation of Remote Unactivated C(sp 3 )−H Bonds: Access to Complex Fluoroalkylated Alkenes
Author(s) -
Wu Shuo,
Wu Xinxin,
Wang Dongping,
Zhu Chen
Publication year - 2019
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.201812927
Subject(s) - regioselectivity , chemistry , radical , hydrogen bond , functional group , double bond , medicinal chemistry , combinatorial chemistry , surface modification , stereochemistry , organic chemistry , catalysis , molecule , polymer
Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C−H bonds is of great synthetic value. Despite advances in radical‐mediated functionalization of C(sp 3 )−H bonds by a hydrogen‐atom transfer process, the site‐selective vinylation of remote C(sp 3 )−H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp 3 )−H bonds. The remote C(sp 3 )−H activation is promoted by a C‐centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri‐/di‐/mono‐fluoromethyl and perfluoroalkyl groups.