Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni’s Reagent

This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl–CF3 products with excellent functional...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 15; pp. 4677 - 4680
Main Authors Chen, Yanchi, Ma, Guobin, Gong, Hegui
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CROSS-COUPLING REACTIONS
DECARBOXYLATIVE TRIFLUOROMETHYLATION
COMPLEXES
SECONDARY
ORGANIC HALIDES
FLUORINATION
ALKYLBORONIC ESTERS
ELECTROPHILES
BROMIDES
BORYLATION
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Summary:This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl–CF3 products with excellent functional group tolerance and broad substrate scope. A mechanism involving a reaction of alkyl–Cu with Togni’s reagent was proposed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02005