Organofluorines have attracted growing interest in recent years. Fluorine-containing molecules have found wide applications in agrochemicals, drug development, and material technology due to unique properties of fluorine atom, i.e. strong electron-withdrawing ability and high hydrophobicity. Therefore, the introduction of fluorine atom and fluorine-containing scaffolds into organic molecules and/or heterocycles gains significant attention and is a crucial strategy in medicine and material research.
In the present work, an effective, simple, and easy to handling method for the direct trifluoromethylthiolation of 2-alkynyl azidoarenes with AgSCF3 was developed. The method provides a straightforward synthesis of 3-((trifluoromethyl)thio)indoles with moderate to high yields in one step and short reaction time. The reaction proceeds through a radical pathway and demonstrated good functional group compatibility.
Jongkonporn Phetcharawetch, Nolan M. Betterley, Vichai Reutrakul, Darunee Soorukram, Pawaret Leowanawat, Chutima Kuhakarn* “Synthesis of 3-((trifluoromethyl)thio)indoles via trifluoromethylthiolation of 2-alkynyl azidoarenes with AgSCF3” Journal of Fluorine Chemistry 2021, 250, 109878.