Decarboxylative thiolation of redox-active esters to free thiols and further diversification

Tianpeng Cao, Tianxiao Xu, Ruting Xu, Xianli Shu and Saihu Liao ()
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Tianpeng Cao: Fuzhou University
Tianxiao Xu: Fuzhou University
Ruting Xu: Fuzhou University
Xianli Shu: Fuzhou University
Saihu Liao: Fuzhou University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Thiols are important precursors for the synthesis of a variety of pharmaceutically important sulfur-containing compounds. In view of the versatile reactivity of free thiols, here we report the development of a visible light-mediated direct decarboxylative thiolation reaction of alkyl redox-active esters to free thiols based on the abundant carboxylic acid feedstock. This transformation is applicable to various carboxylic acids, including primary, secondary, and tertiary acids as well as natural products and drugs, forging a general and facile access to free thiols with diverse structures. Moreover, the direct access to free thiols affords an advantage of rapid in situ diversification with high efficiency to other important thiol derivatives such as sulfide, disulfide, thiocyanide, thioselenide, etc.

Date: 2020
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DOI: 10.1038/s41467-020-19195-w

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