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Org Lett. 2019 Aug 16;21(16):6347-6351. doi: 10.1021/acs.orglett.9b02236. Epub 2019 Aug 2.

Transition-Metal-Free ipso-Trifluoromethylthiolation of Lithium Aryl Boronates.

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Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry , Nankai University , Tanjin 300071 , China.
Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.


A transition-metal-free direct trifluoromethylthiolation of the ipso-carbon of lithium aryl boronates with trifluoromethanesulfenate under mild conditions was described. In addition, late-stage site-selective C-H borylation/trifluoromethylation and C-Cl borylation/trifluoromethylthiolation of biologically active molecules was developed. Initial mechanistic study suggested that the Li+ cation plays a vital role by coordinating to the oxygen atom of an aryl boronate complex and the oxygen of the reagent, thus allowing the aryl group to directly attack the trifluoromethylthio group of the trifluoromethylthiolating reagent.

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