Defluorinative Alkylation of Trifluoromethyl Alkenes with Soft Carbon Nucleophiles Enabled by a Catalytic Amount of Base

Direct manipulation of readily accessible trifluoromethyl alkenes (TAs) represents an attractive approach to the preparation of diversified fluorine‐containing compounds. In this study, defluorinative alkylation reactions of TAs with a broad array of soft carbon nucleophiles have been documented. Nu...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-07, Vol.364 (13), p.2241-2247
Main Authors: Gao, Ya, Qin, Wei, Tian, Ming‐Qing, Zhao, Xuefei, Hu, Xu‐Hong
Format: Article
Language:English
Subjects:
2-fluoro-4H-pyrans
Alkenes
Alkylation
Base metal
Carbon
Defluorination
Ductile-brittle transition
Ethers
Fluorine
gem-difluoroalkenes
Nucleophiles
Reagents
soft nucleophiles
Transition metals
trifluoromethyl alkenes
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Summary:Direct manipulation of readily accessible trifluoromethyl alkenes (TAs) represents an attractive approach to the preparation of diversified fluorine‐containing compounds. In this study, defluorinative alkylation reactions of TAs with a broad array of soft carbon nucleophiles have been documented. Nucleophilic substitutions occur enabled by a catalytic amount of base, providing access to tertiary alkyl substituted gem‐difluoroalkenes and 2‐fluoro‐4H‐pyrans. By extending the nucleophiles to silyl enol ethers, defluorination can be achieved in the absence of base to give gem‐difluoroalkenes. This process, which eliminates the requirement of organometallic reagents, transition metals, or strong bases for the C−F bond cleavage, is applicable to late‐stage modification of complex molecules.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200328