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TETRAHEDRON · 2024 · IF 2.1

An efficient method for thioesterification of carboxylic acid with sulfenylchloride

Jiahong Chen,Mengke Wang,Weichun Huang,You Zi

A mild and convenient method for synthesizing thioesters has been developed, from sulfenylchlorides and carboxylic acids via a phosphine mediated umpolung process. This approach efficiently produces a broad spectrum of thioesters from readily available carboxylic acids, including primary, secondary, and tertiary types, as well as bioactive molecules. The successful gram-scale reactions also validate its scalability and practical application.

研究领域: 有机化学 · 药物化学

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JOURNAL OF ORGANIC CHEMISTRY · 2020 · IF 4.335

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides

Shimin Xie,Lebin Su,Min Mo,Wang Zhou,Yongbo Zhou,Jianyu Dong

An alternative thioesterification reaction via copper-catalyzed oxidative coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivatives and the products. The reaction produces various thioesters in good to excellent yields with good functional group tolerance. In the reaction, stable and easily available aroylhydrazides are used as acyl sources and the relatively odorless disulfides are used as S sources. Mechanistic investigations demonstrate that the reaction of copper salt and oxidant (NH4)2S2O8 allows for achievement of tandem processes, including deprotonation, free-radical-mediated denitrogenation, and C–S bond formation.

研究领域: 有机化学 · 催化反应

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An efficient method for thioesterification of carboxylic acid with sulfenylchloride

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides