Transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles with sodium trifluoromethanesulfinates in ionic liquids. (27th April 2021)

• Record Type: Journal Article
• Authors: Wang, Fei; Lu, Guo-Ping; Lin, Yamei
• Is Part Of: Tetrahedron letters. Volume 70(2021)
• Publication Date: 2021-04-27
• Subjects: Electrophilic trifluoromethylthiolation -- Indole -- Sodium trifluoromethanesulfinates -- Imidazolium-based ionic liquid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Stable and easy-to-handle CF3 SO2 Na was applied for the direct trifluoromethylthiolation. A transition-metal- and phosphorus-free protocol for trifluoromethylthiolation of indoles. Ionic liquid acts as reducing agents and recyclable solvent in this transformation. Abstract: An acid-promoted protocol has been developed to achieve the transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles using sodium trifluoromethanesulfinates in an imidazolium-based ionic liquid ([Hmim]Br). [Hmim]Br not only acts as a recyclable solvent, but also as the reductant in this transformation. The advantages of this chemistry include simple operation, use of a recyclable solvent, avoidance of transition-metal and phosphorus, and gram-scale synthesis.