Issue 4, 2024

Dithiocarbamate mediated thioamidation via C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations

Abstract

Dithiocarbamate salts have been explored in a novel C–C thioamidation of styrene in the presence of ammonium persulfate and molecular oxygen. A series of thioamide compounds with different structural variations have been prepared in good yields. Various cyclic/acyclic secondary amine, aromatic amine, benzylamine and amino acid based thioamides have been prepared following the protocol. The protocol has further been applied to decarbonylative thioamidation of benzaldehyde and toluene and decarboxylative thioamidation of benzoic acid. The reaction mechanism has been proposed by isolation of the reaction intermediate and GC-MS analysis of the reaction mixture. The post-synthetic potential of the synthesized thioamide has been checked through a C–C cross-coupling reaction via C–N bond cleavage.

Graphical abstract: Dithiocarbamate mediated thioamidation via C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations

Supplementary files

Article information

Article type
Research Article
Submitted
20 Nov 2023
Accepted
21 Dec 2023
First published
22 Dec 2023

Org. Chem. Front., 2024,11, 1150-1156

Dithiocarbamate mediated thioamidation via C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations

D. Patra and A. Saha, Org. Chem. Front., 2024, 11, 1150 DOI: 10.1039/D3QO01921G

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