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

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Title Elusive Thiyl Radical Migration in a Visible Light Induced
Chemoselective Rearrangement of g-Keto Acrylate Thioesters:
Synthesis of Substituted Butenolides
 
Creator Naskar, Sandip
Das, Indrajit
 
Subject Chemistry
 
Description 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.
 
Publisher John Wiley & Sons
 
Date 2017-03-06
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2645/1/ADVANCED_SYNTHESIS_%26_CATALYSIS_%2C2017.pdf
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
 
Relation http://dx.doi.org/10.1002/adsc.201601016
http://www.eprints.iicb.res.in/2645/