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Nickel‐Catalyzed Three‐Component Coupling Reaction of Tetrafluoroethylene and Aldehydes with Silanes via Oxa‐Nickelacycles
Author(s) -
Shirataki Hiroshi,
Ohashi Masato,
Ogoshi Sensuke
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801721
Subject(s) - chemistry , silanes , tetrafluoroethylene , aldehyde , catalysis , deprotonation , nickel , silylation , organic chemistry , coupling reaction , fluorine , lewis acids and bases , polymer chemistry , stoichiometry , copolymer , silane , polymer , ion
The nickel‐catalyzed synthesis of a variety of fluorine‐containing silyl ethers from tetrafluoroethylene (TFE) and aldehydes with silanes in a selective manner is disclosed. Stoichiometric reactions revealed that the oxa‐nickelacycle, which is generated upon oxidative cyclization of TFE and an aldehyde with Ni 0 , is the key intermediate, whose molecular structure was confirmed by single‐crystal X‐ray diffraction analysis. In order to demonstrate the synthetic utility of this procedure, one of the reaction products was transformed into trifluorovinyl and organic silicon compounds via deprotonation with a Lewis base.