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

Nat Commun

Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, 350108, Fuzhou, China.

Published: October 2020

AI Article Synopsis

  • Thiols serve as key building blocks for creating various important sulfur-containing pharmaceuticals.
  • The study introduces a new method that uses visible light to directly convert alkyl redox-active esters into free thiols using carboxylic acids.
  • This method allows easy access to a range of free thiol structures and enables efficient transformation into other thiol derivatives like sulfides and disulfides.

Article 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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7578659PMC
http://dx.doi.org/10.1038/s41467-020-19195-wDOI Listing

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