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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Published inAngewandte Chemie Vol. 131; no. 41; pp. 14757 - 14761
Main Authors Ye, Fei, Berger, Florian, Jia, Hao, Ford, Joseph, Wortman, Alan, Börgel, Jonas, Genicot, Christophe, Ritter, Tobias
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 07.10.2019
Subjects
Aromatic compounds
C-H-Funktionalisierung
Chemistry
Coupling (molecular)
Functional groups
Organic chemistry
Photoredoxkatalyse
Reagents
Regioselektivität
Salts
Sulfonium salts
Sulfoniumsalze
Trifluormethylierung
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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. Das Beste zum Schluss: Eine positionsselektive Trifluormethylierung von Arenen verläuft über Arylsulfonium‐Salze als Intermediate. Viele funktionelle Gruppen werden in dieser Reaktion toleriert, die zudem die Synthese von C2F5‐Derivaten wirkstoffähnlicher Verbindungen ermöglicht.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201906672