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Selective C–F Bond Allylation of Trifluoromethylalkenes
Author(s) -
Zhu Chuan,
Sun MengMeng,
Chen Kai,
Liu Haidong,
Feng Chao
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.202106531
Subject(s) - nucleophile , surface modification , chemistry , moiety , combinatorial chemistry , selectivity , stereochemistry , bond cleavage , nucleophilic addition , molecule , medicinal chemistry , organic chemistry , catalysis
Selective C−F bond functionalization of CF 3 group represents an appealing strategy for the incorporation of pharmaceutically privileged difluoromethylene moiety. Despite the recent significant advancement attained in the functionalization of Ar‐CF 3 molecules, prescriptions amenable for alkenyl‐CF 3 congeners remain sufficiently inadequate. Herein, we report a strategically novel protocol for the C−F bond elaboration of trifluoromethylalkene derivatives. By using readily available allyl metallics as nucleophilic coupling partner, the present reaction enables an expedient construction of structurally diversified CF 2 ‐bridged 1,5‐dienes. Furthermore, the exquisite selectivity observed in this transformation is revealed to be based on the underlying mechanism that consists of a cascade of nucleophilic S N 2′ defluorinative allylation and electronically promoted Cope rearrangement.