Access to 2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed Intramolecular Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes
A novel Pd(0)-catalyzed intramolecular 5-<i>exo</i>-<i>dig</i> cyclization between trifluoroacetimidoyl halides and alkynes has been established, involving a key alkyne oxypalladation process with H<sub>2</sub>O serving as the nucleophile. This protocol exhibits broad functional group tolerance under mild conditions, providing 2-(trifluoromethyl)indole derivatives in moderate to excellent yields. Notably, the streamlined synthesis of a trifluoromethylated pravadoline analogue and the anticancer bioactivities of three products highlight the potential of this methodology for practical applications.
Authors
- Chunjie Ni (ORCID: https://orcid.org/0000-0003-1479-5484)
- Yantao Zhu (ORCID: https://orcid.org/0000-0001-7460-6265)
- Xiaojuan Xu (ORCID: https://orcid.org/0000-0003-1869-930X)
- Chen Chen (ORCID: https://orcid.org/0000-0002-5388-9611)
- Yining Zhao (ORCID: https://orcid.org/0000-0002-7851-0890)
- Zhanhang Liang
Institutions
- Nanjing Tech University (CN)
- Tianjin Normal University (CN)
- Yancheng Teachers University (CN)
- Pharmaceutical Biotechnology (Czechia) (CZ)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-06
- DOI
- https://doi.org/10.1021/acs.orglett.5c01642
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province