Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids

Copper-catalyzed decarboxylative difluoroalkylation and perfluoroalkylation of α,β-unsaturated carboxylic acids is described. Promoted by dialkyl phosphite, this novel reaction affords fluoroalkylated motifs with excellent stereoselectivity and broad substrate scope under mild reaction conditions fr...

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Published inJournal of organic chemistry Vol. 82; no. 1; pp. 597 - 605
Main Authors Lai, Yin-Long, Lin, Dian-Zhao, Huang, Jing-Mei
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.01.2017
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Summary:Copper-catalyzed decarboxylative difluoroalkylation and perfluoroalkylation of α,β-unsaturated carboxylic acids is described. Promoted by dialkyl phosphite, this novel reaction affords fluoroalkylated motifs with excellent stereoselectivity and broad substrate scope under mild reaction conditions from readily available fluoroalkyl iodides and bromides. Preliminary mechanism study suggests that radical pathway was involved in the catalytic cycle and dialkyl phosphite had played an indispensable role in this reaction.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02613