Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines

Yibin Ye, Kelvin Pak Shing Cheung, Lisi He and Gavin Chit Tsui*

*Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, Email: gctsuicuhk.edu.hk

Y. Ye, K. P. S. Cheung, L. He, G. C. Tsui, Org. Lett., 2018, 20, 1676-1679.

DOI: 10.1021/acs.orglett.8b00509

---

Abstract

The use of the well-established fluoroform-derived CuCF₃ reagent enables the synthesis of 2-(trifluoromethyl)indoles from easily accessible 2-alkynylanilines via a domino trifluoromethylation/cyclization strategy. 3-formyl-2-(trifluoromethyl)indoles can also be synthesized, which are useful intermediates for the preparation of trifluoromethylated drug analogues.

see article for more examples

proposed mechanism

---

---

Key Words

indoles, trifluoromethylation, oxygen

---

ID: J54-Y2018