Carbosulfonylation of Alkynes: A Direct Conversion of sp‑C to sp3‑C through Visible Light-Mediated 3‑Component Reaction

A 3-component metal-free carbo­sulfonylation of alkynes is reported using readily available alkyl carboxylic acids and arylsulfinates under visible light irradiation. This photochemical approach gives direct conversion of sp-C to sp3-C yielding highly functionalized alkyl sulfones. It employs feedst...

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Published inOrganic letters Vol. 26; no. 37; pp. 7858 - 7863
Main Authors Bhargava Reddy, Mandapati, Becker, Vanessa E., McGarrigle, Eoghan M.
Format Journal Article
LanguageEnglish
Published American Chemical Society 20.09.2024
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Letter
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Summary:A 3-component metal-free carbo­sulfonylation of alkynes is reported using readily available alkyl carboxylic acids and arylsulfinates under visible light irradiation. This photochemical approach gives direct conversion of sp-C to sp3-C yielding highly functionalized alkyl sulfones. It employs feedstock chemicals as starting materials and shows a broad substrate scope and moderate diastereo­selectivity. The method’s utility is highlighted in the synthesis of sedum alkaloids. A single photocatalyst is proposed to be active in two distinct photocatalytic cycles operating in tandem.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02700