Radical C−H Bond Trifluoromethylation of Alkenes by High‐Valent Copper(III) Trifluoromethyl Compounds

A general and selective method is developed that allows direct vinylic C−H bond trifluoromethylation of 1,1‐diarylalkenes by a high‐valent copper(III) trifluoromethyl complex, producing biologically active trifluoromethylated alkenes (as well as trifluoromethylated carbocyclic compounds). This funda...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-12, Vol.361 (23), p.5305-5310
Main Authors: Zhang, Hao‐Ran, Xiao, Chang, Zhang, Song‐Lin, Zhang, Xiaoming
Format: Article
Language:English
Subjects:
Alkenes
Chemical compounds
Coordination compounds
Copper
Copper compounds
Cu(III)−CF3 compounds
C−H activation
Electron transfer
Hydrogen bonds
Noble metals
Organic chemistry
Oxidizing agents
Single electrons
Tertiary amine
Trifluoromethylated alkenes
Trifluoromethylation
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Summary:A general and selective method is developed that allows direct vinylic C−H bond trifluoromethylation of 1,1‐diarylalkenes by a high‐valent copper(III) trifluoromethyl complex, producing biologically active trifluoromethylated alkenes (as well as trifluoromethylated carbocyclic compounds). This fundamental reactivity of Cu(III)−CF3 compounds has thus far been unknown. The presence of a tertiary amine is crucial to this reaction, acting as both a weak base and a single electron transfer (SET) promoter to the vinylic hydrogen. This method starts from bulk olefins under cost‐effective conditions (without the need for external noble metal photocatalyst or stoichiometric amounts of oxidant), and thus is valuable for practical and sustainable applications.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901105