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Multicomponent Synthesis of Biologically Relevant S-Aryl Dithiocarbamates Using Diaryliodonium Salts

Sushanta K. Parida, Sonal Jaiswal, Priyanka Singh* and Sandip Murarka*

*Indian Institute of Technology Jodhpur, Karwar 342037, Rajasthan, India, Email: priyankasinghiitj.ac.in, sandipmurarkaiitj.ac.in

S. K. Parida, S. Jaiswal, P. Singh, S. Murarka, Org. Lett., 2021, 23, 6401-6406.

DOI: 10.1021/acs.orglett.1c02220


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Abstract

An efficient transition-metal-free one-pot three-component reaction between diaryliodonium triflates, cyclic and acyclic aliphatic amines, and carbon disulfide provides biologically relevant S-aryl dithiocarbamates in good yields under mild conditions. This methodology is robust, scalable, and exhibits a broad substrate scope.

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General procedure (GP) for the synthesis of S-aryl dithiocarbamates

A screw-cap vial was charged with CS2 (0.625 mmol, 2.5 equiv) in DCM (2.5 mL) and respective amines (0.3 mmol, 1.2 equiv ) were added dropwise at room temperature. After 5 min of stirring the resulting solution, diaryliodonium salts (0.25 mmol, 1 equiv) were added portion-wise over 10-15 minutes and the reaction mixture was continued to stir at room temperature till completion (2-4 h). After completion, the reaction mixture was concentrated under vacuum and the crude residue was purified by column chromatography (5-20% Ethyl acetate in hexane) to yield the corresponding products 3.


Key Words

dithiocarbamates, multcomponent reactions


ID: J54-Y2021