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Synthesis 2024; 56(24): 3769-3778
DOI: 10.1055/a-2350-1248
DOI: 10.1055/a-2350-1248
paper
Recent Advancements in the Chemistry of Diazo Compounds
Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols
This work was supported by the Science and Engineering Research Board (CRG/2023/000584).
Abstract
A visible-light-induced multicomponent reaction of vinyl sulfoxonium ylide, thiol, and diazo ester to generate tertiary sulfide is described. The present diastereoselective gem-difunctionalization of the diazo ester can be achieved under mild conditions, as it does not require any additives, catalysts, or transition metals and is tolerant of air and moisture. Due to more nucleophilicity, vinyl sulfoxonium ylide undergoes S–H insertion with thiols to generate an allyl sulfide intermediate. Simultaneously, diazo ester undergoes photolysis to generate a carbene intermediate. Subsequently, the coupling of carbene and allyl sulfide intermediates generates sulfonium ylide, which undergoes Doyle–Kirmse rearrangement to generate tertiary sulfide scaffolds.
Key words
visible light mediated reaction - metal-free transformation - carbenes - diazoacetates - sulfur ylides - sigmatropic rearrangement - stereoselective synthesis.Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2350-1248.
- Supporting Information
Publication History
Received: 08 May 2024
Accepted after revision: 21 June 2024
Accepted Manuscript online:
21 June 2024
Article published online:
15 July 2024
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