Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CF₃SiMe₃ and Elemental Sulfur or AgSCF₃ and KBr with Amines

Long Zhen, Hui Fan, Xiaoji Wang, Liqin Jiang*

*School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China, Email: lqjiangsat.ecnu.edu.cn

L. Zhen, H. Fan, X. Wang, L. Jiang, Org. Lett., 2019, 21, 2106-2110.

DOI: 10.1021/acs.orglett.9b00383

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Abstract

Reactions of thiocarbonyl fluoride derived from CF₃SiMe₃, elemental sulfur, and KF with secondary amines provides a wide variety of thiocarbamoyl fluorides in good yields at room temperature in THF, whereas the reaction with primary amines gives isothiocyanates. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF₃ can be used as an alternative.

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Key Words

Isothiocyanates, Multicomponent Reactions, Thiocarbamoyl Halides

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ID: J54-Y2019