Trifluoromethyl Group (CF<sub>3</sub>) Induced Regioselective Larock Indole Synthesis from Unsymmetric β-CF<sub>3</sub>-1,3-enynes
The indole skeleton exists widely in natural products, pharmaceuticals, and materials. We disclose here a trifluoromethyl group induced regioselective Larock indole synthetic method from unsymmetric 2-CF<sub>3</sub>-1,3-enynes. The presence of a trifluoromethyl group is determinable for the regioselectivity. Once the CF<sub>3</sub> group was replaced with the methyl or phenyl group, a ratio of 1:1 to 1:1.4 isomers were obtained. This strategy features good regioselectivity, broad substrate scope, and high functional group tolerance. The protocol reported here offers an alternative solution to the rare 3,4-functionalization of 2-CF<sub>3</sub>-1,3-enynes. The products were further transformed to show distinctive reactivity in hydroboration-oxidation and hydro-bromination.
Authors
- Xiangjun Peng (ORCID: https://orcid.org/0000-0003-0715-7919)
- Daohong Yu (ORCID: https://orcid.org/0000-0003-4840-9051)
- Wen‐Hao Shao
- Wenjun Luo (ORCID: https://orcid.org/0009-0000-8862-7251)
- Yan‐Hua Qiu
- Yongshun Wen
- Zhenjun Huang (ORCID: https://orcid.org/0009-0000-1474-2388)
- C.H. Huang
- Peng-Xiang Ma
- Lipeng Long
Institutions
- Gannan Medical University (CN)
- Gannan Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00501
- Citations
- 5
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 3.95
Funders
- Graduate Innovative Special Fund Projects of Jiangxi Province
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangxi Province
- Gannan Normal University