Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols

Synthesis Pub Date : 2024-07-15 DOI:10.1055/a-2350-1248
Srashti Bhardwaj, Raju Sen, Payel Adhikari, Janakiram Vaitla
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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.

Abstract Image

可见光介导的重氮化合物与乙烯基锍酰化物和硫醇的双官能化作用
本研究描述了乙烯基砜、硫醇和重氮酯在可见光诱导下发生多组分反应生成叔硫醚的过程。这种重氮酯的非对映选择性 gem-二官能化反应可以在温和的条件下实现,因为它不需要任何添加剂、催化剂或过渡金属,并且对空气和湿气有耐受性。由于亲核性较强,乙烯基砜酰亚胺会与硫醇发生 S-H 插入反应,生成烯丙基硫醚中间体。同时,重氮酯发生光解,生成碳烯中间体。随后,碳烯和烯丙基硫醚中间体耦合生成锍酰亚胺,锍酰亚胺经过多伊尔-基尔梅斯重排生成三硫化物支架。
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