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- Title
Visible‐Light Induced Trifluoromethylation/Cyclization of Unactivated Alkene‐Bound Quinazolinones.
- Authors
Zou, Luqian; Zhao, Hengyuan; Wang, Xinming; Dong, Jun; Yang, Chungang; Sun, Weiqing; Xu, Jianbin; Fan, Baomin
- Abstract
Herein, we reported a selective, mild method for the visible‐light‐photocatalyzed trifluoromethylation and cyclization of unactivated tethered alkenes to provide tri‐ and tetracyclic quinazolinones. Trifluoroacetic acid and anhydride are inexpensive and readily available reagents for the process that proceeds without the addition of a strong oxidant. The wide substrate scope and the formation of 5‐ and 6‐membered rings are demonstrated in 44–82 % yields. Control experiments provide the basis for a proposed mechanism involving photocatalyzed SET from fac‐Ir(ppy)3 to TFAA and trifluoromethyl radical‐mediated regioselective cyclization. The practicality of the protocol was illustrated by a gram‐scale synthesis in 76 % yield.
- Subjects
QUINAZOLINONES; RING formation (Chemistry); FREE radical reactions; TRIFLUOROACETIC acid
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 17, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400056