Copper-Catalyzed Radical Aminotrifluoromethylation of Alkenes

We report herein an unprecedented protocol for aminotrifluoromethylation of alkenes. With Cu­(OTf)2 as the catalyst, the reaction of alkenes, (bpy)­Zn­(CF3)2, and N-fluorobis­(benzene­sulfonyl)­imide (NFSI) at room temperature provides the corresponding aminotrifluoro­methylation products in satisfa...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 29; pp. 11440 - 11445
Main Authors Xiao, Haiwen, Shen, Haigen, Zhu, Lin, Li, Chaozhong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.07.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
REAGENT
GABA
OLEFINS
TRIFLUOROMETHYLATION REACTIONS
GENERATION
DRIVEN
ACCESS
UNACTIVATED ALKENES
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Summary:We report herein an unprecedented protocol for aminotrifluoromethylation of alkenes. With Cu­(OTf)2 as the catalyst, the reaction of alkenes, (bpy)­Zn­(CF3)2, and N-fluorobis­(benzene­sulfonyl)­imide (NFSI) at room temperature provides the corresponding aminotrifluoro­methylation products in satisfactory yields with high regioselectivity opposite to those driven by CF3 radical addition. The method exhibits a broad substrate scope and wide functional group compatibility. A mechanism involving N-radical addition to alkenes followed by trifluoromethylation of alkyl radicals is proposed.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06141