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Radical C−H Bond Trifluoromethylation of Alkenes by High‐Valent Copper(III) Trifluoromethyl Compounds
Author(s) -
Zhang HaoRan,
Xiao Chang,
Zhang SongLin,
Zhang Xiaoming
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901105
Subject(s) - trifluoromethylation , chemistry , trifluoromethyl , copper , reactivity (psychology) , amine gas treating , medicinal chemistry , organic chemistry , combinatorial chemistry , photochemistry , alkyl , medicine , alternative medicine , pathology
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)−CF 3 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 abstract 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.