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Stereoselective Palladium‐Catalyzed C−F Bond Alkynylation of Tetrasubstituted gem ‐Difluoroalkenes
Author(s) -
Ma Qiao,
Wang Yanhui,
Tsui Gavin Chit
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202002219
Subject(s) - stereoselectivity , chemistry , alkynylation , palladium , moiety , alkene , catalysis , conjugated system , stereochemistry , oxidative addition , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer
A stereoselective Pd(PPh 3 ) 4 ‐catalyzed C−F bond alkynylation of tetrasubstituted gem ‐difluoroalkenes with terminal alkynes has been developed. This method gives access to a great variety of conjugated monofluoroenynes bearing a tetrasubstituted alkene moiety with well‐defined stereochemistry. Chelation‐assisted oxidative addition of Pd to the C−F bond is proposed to account for the high level of stereocontrol. An X‐ray crystal structure of a key monofluorovinyl Pd II intermediate has been obtained for the first time as evidence for the proposed mechanism.