Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions. Issue 7 (28th February 2023)

• Record Type: Journal Article
• Authors: Patra, Debabrata; Saha, Amit
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 7(2023)
• Page Start: 1686
• Page End: 1693
• Publication Date: 2023-02-28
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d3qo00032j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Dithiocarbamates are explored in decarboxylative–decarbonylative thioamidation of arylglyoxylic acids in the presence of Pd-catalyst. Cleavage of two C–C bonds and one C–S bond occurs along with the formation of a new C–C bond in a single strategy. Abstract : Arylglyoxylic acids have been employed in a novel decarboxylative–decarbonylative thioamidation reaction with dithiocarbamate intermediates prepared in situ by the prompt reaction of amines and carbon disulfide. A series of thioamide compounds were synthesized using different arylglyoxylic acids, various secondary amines, a primary amine, aniline, and an amino acid derivative. The reaction is proposed to proceed via an acyl radical intermediate in the presence of a persulfate oxidant and a Pd(ii )-catalyst.