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One-pot Synthesis of Thioesters With Sodium Thiosulfate as a Sulfur Surrogate Under Transition Metal-Free Conditions

One-pot Synthesis of Thioesters With Sodium Thiosulfate as a Sulfur Surrogate Under Transition Metal-Free Conditions

Yen-Sen Liao, Chien-Fu Liang

Org Biomol Chem. 2018 Mar 14;16(11):1871-1881.

PMID: 29473084

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10102177-B	Sodium thiosulfate pentahydrate		10102-17-7	Price

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