Vanadium-Catalyzed Trifluoromethylation/Cyclization of Alkenes and 1,7-Enynes with Togni-II Reagent to Access Trifluoromethylated Oxindoles, Isoquinoline-1,3-diones, and Indeno[1,2-<i>c</i>]quinolines
A vanadium-catalyzed radical cascade trifluoromethylation/(bi)cyclization of alkenes and 1,7-enynes with Togni-II reagent for the synthesis of trifluoromethylated oxindoles, isoquinoline-1,3-diones, and indeno[1,2-<i>c</i>]quinolines has been developed. These transformations show broad substrate compatibility and high regioselectivity. Mechanistic studies reveal that a CF<sub>3</sub> radical is <i>in situ</i> generated to trigger the ensuing 5-<i>exo</i> and 6-<i>exo</i> cyclization, as well as the cascade 6-<i>exo</i>/5-<i>endo</i> bicyclization processes.
Authors
- Lei Zhang (ORCID: https://orcid.org/0000-0003-0614-2651)
- Shaodan Li (ORCID: https://orcid.org/0000-0001-5908-4999)
- Jin-Jin Zhao
- Mengdi Liu (ORCID: https://orcid.org/0000-0001-6499-3126)
Institutions
- Analysis and Testing Centre (CN)
- Hebei Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-29
- DOI
- https://doi.org/10.1021/acs.joc.5c00911
- Citations
- 2
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.58
Funders
- National Natural Science Foundation of China
- Hebei Normal University
- Natural Science Foundation of Hebei Province