Copper-catalyzed radical trifluoroethylthiolation of arylboronic acids with PhSO2SCH2CF3. (2nd March 2022)

• Record Type: Journal Article
• Authors: Dong, Lefeng; Liang, Junqing; Chen, Ruijia; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong
• Is Part Of: Tetrahedron letters. Volume 92(2022)
• Publication Date: 2022-03-02
• Subjects: Cu-catalyst -- Radical reaction -- Trifluoroethylthiolation -- Fluorine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153293
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Trifluoroethylthio group (SCH2 CF3 ) is a key functionality in several pharmaceutical and agrochemical compounds, the methods for the installation of the 2, 2, 2-trifluoroethylthio group are sought after. Herein, we report a copper-catalyzed trifluoroethylthiolation reaction of S-(2, 2, 2-trifluoroethyl) benzenesulfonothioates and phenylboronic acids at room temperature. The reaction achieved the insertion of trifluoroethylthio moiety to efficiently obtain various substituted aryl 2, 2, 2-trifluoroethyl thioethers in good yields. Mechanistic investigation indicates the trifluoroethylthiolation radical is involved in the catalytic circle. Moreover, trifluoroethylthiolated clofibrate was synthesized in a particular fashion.