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NiH‐Catalyzed Migratory Defluorinative Olefin Cross‐Coupling: Trifluoromethyl‐Substituted Alkenes as Acceptor Olefins to Form gem ‐Difluoroalkenes
Author(s) -
Chen Fenglin,
Xu Xianfeng,
He Yuli,
Huang Genping,
Zhu Shaolin
Publication year - 2020
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.201915840
Subject(s) - trifluoromethyl , substituent , olefin fiber , chemistry , intermolecular force , migratory insertion , catalysis , acceptor , chemoselectivity , photochemistry , coupling (piping) , electron acceptor , medicinal chemistry , organic chemistry , alkyl , molecule , materials science , physics , metallurgy , condensed matter physics
We report a NiH‐catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron‐deficient trifluoromethyl substituent in both intra‐ and intermolecular fashion to form gem ‐difluoroalkenes. This migratory coupling shows both site‐ and chemoselectivity under mild conditions, with the formation of a tertiary or quaternary carbon center.