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- Title
Late‐Stage Modification of Drugs via Alkene Formal Insertion into Benzylic C−F Bond.
- Authors
Wang, Jing; Wang, Yahui; Liang, Yan; Zhou, Liejin; Liu, Lijuan; Zhang, Zuxiao
- Abstract
C−F insertion of carbon‐atom units is underdeveloped although it poses significant potential applications in both drug discovery and development. Herein, we report a photocatalytic protocol for late‐stage modification of trifluoromethyl aromatic drugs involving formal insertion of abundant alkene feedstocks into a benzylic C−F bond selectively. This redox‐neutral transformation features mild conditions and extraordinary functional group tolerance. Preliminary studies are consistent with this transformation involving a radical‐polar crossover pathway. Additionally, it offers an alternative strategy for difunctionalization of alkenes via quenching of the carbocation intermediate with nucleophiles other than external fluoride.
- Subjects
ALKENES; DRUG discovery; FUNCTIONAL groups; DRUG development; NUCLEOPHILES; CARBOCATIONS
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 5, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202215062