Synthesis of thioesters using an electrochemical three-component reaction involving elemental sulfur

An electrochemical three-component reaction involving elemental sulfur is disclosed for achieving a metal-free, oxidant-free synthesis of thioesters in a high atom-economical, step-economical and chemoselective manner. A mechanistic investigation indicates that the use of elemental sulfur to trap ac...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-06, Vol.6 (48), p.6154-6157
Main Authors: Liu, Gongbo, Xu, Shuoyu, Yue, Yangyang, Su, Changhui, Song, Wangze
Format: Article
Language:English
Subjects:
Carbonyls
Oxidizing agents
Sulfur
Synthesis
Thioesters
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Summary:An electrochemical three-component reaction involving elemental sulfur is disclosed for achieving a metal-free, oxidant-free synthesis of thioesters in a high atom-economical, step-economical and chemoselective manner. A mechanistic investigation indicates that the use of elemental sulfur to trap acyl radical derived from radical umpolung of α-keto acid with an electrochemical design can efficiently generate a carbonyl thiyl radical, which can further be captured by diazoalkane to afford various thioesters. An electrochemical three-component reaction involving elemental sulfur is disclosed for achieving a metal-free, oxidant-free synthesis of thioesters in a high atom-economical, step-economical and chemoselective manner.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc01910e