Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Incorporation of the CF3 group into arenes has found increasing importance in drug discovery. Herein, we report the first photoredox‐catalyzed cross‐coupling of aryl thianthrenium salts with a copper‐based trifluoromethyl reagent, which enables a site‐selective late‐stage trifluoromethylation of are...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-10, Vol.58 (41), p.14615-14619
Main Authors: Ye, Fei, Berger, Florian, Jia, Hao, Ford, Joseph, Wortman, Alan, Börgel, Jonas, Genicot, Christophe, Ritter, Tobias
Format: Article
Language:English
Subjects:
Aromatic compounds
Communication
Communications
Coupling (molecular)
Functional groups
late-stage C−H functionalization
Organic chemistry
photoredox catalysis
Reagents
Salts
site selectivity
Sulfonium salts
trifluoromethylation
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Summary:Incorporation of the CF3 group into arenes has found increasing importance in drug discovery. Herein, we report the first photoredox‐catalyzed cross‐coupling of aryl thianthrenium salts with a copper‐based trifluoromethyl reagent, which enables a site‐selective late‐stage trifluoromethylation of arenes. The reaction proceeds with broad functional group tolerance, even for complex small molecules on gram scale. The method was further extended to produce pentafluoroethylated derivatives. Save the best for last: A site‐selective late‐stage trifluoromethylation of arenes proceeds via aryl sulfonium salts. The reaction features broad functional group tolerance and also enables the generation of C2F5 derivatives of drug‐like compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201906672