One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions. Issue 11 (23rd February 2018)

• Record Type: Journal Article
• Authors: Liao, Yen-Sen; Liang, Chien-Fu
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 11(2018)
• Page Start: 1871
• Page End: 1881
• Publication Date: 2018-02-23
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00178b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We have developed a one-pot reaction to provide thioester derivatives via sodium thiosulfate as a sulfur source under transition metal-free conditions. Abstract : In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%–90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.