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Updated: May 24, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Visible-Light-Induced Trifluoromethyl Radical Addition to Thiocarbonyl of Thioamide Derivatives
Yuanyuan Ren1, Yuxiu Zhou1, Ke-Hu Wang1
1College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. China.
Abstract:
An effective trifluoromethyl radical addition to the thiocarbonyl of thioamide derivatives is described, which produces various trifluoromethylthiolated N-heterocycles such as 6-(trifluoromethylthio)phenanthridine, 2-(trifluoromethylthio)indole, and 2-(trifluoromethylthio)benzothiazole derivatives under visible-light irradiation. The process features advantages such as mild reaction conditions, a cheap and easily available trifluoromethyl source (CF3Br), and green energy, as well as broad substrate scope. The reaction mechanism is investigated in detail, and scale-up experiments are performed.
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