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Nat Commun ; 11(1): 5340, 2020 10 21.
Article in English | MEDLINE | ID: mdl-33087708

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.


Subject(s)
Sulfhydryl Compounds/chemistry , Sulfhydryl Compounds/chemical synthesis , Drug Discovery , Esters/chemical synthesis , Esters/chemistry , Models, Chemical , Molecular Structure , Oxidation-Reduction , Protein Processing, Post-Translational , Small Molecule Libraries
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