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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 (free Supporting Information)


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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


ID: J54-Y2019