Elusive Thiyl Radical Migration in a Visible Light Induced Chemoselective Rearrangement of g-Keto Acrylate Thioesters: Synthesis of Substituted Butenolides

Naskar, Sandip and Das, Indrajit (2017) Elusive Thiyl Radical Migration in a Visible Light Induced Chemoselective Rearrangement of g-Keto Acrylate Thioesters: Synthesis of Substituted Butenolides. Advanced Synthesis & Catalysis, 359 (5). pp. 875-885. ISSN 1615-4150

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    Abstract

    The first metal/photocatalyst-free, visible light induced chemoselective rearrangement of gketo acrylate thioesters via elusive thiyl radical migration is described. Thioesters bearing at least one alkyl substitution undergo 1,2-thiyl radical migration, whereas 1,4-migration has been observed when the substrate is substituted by aromatics only. The reactions show excellent functional group tolerance and are proposed to proceed through the trans-cis isomerization/intramolecular lactonization/thiyl radical capture pathway. This atom-economical process constitutes an efficient and practical method for the formation of substituted butenolides.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/2645
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Ms Sutapa Ganguly
    Date Deposited: 12 May 2017 13:22
    Last Modified: 16 May 2017 13:25
    Official URL: http://dx.doi.org/10.1002/adsc.201601016
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