Elusive Thiyl Radical Migration in a Visible Light Induced Chemoselective Rearrangement of g-Keto Acrylate Thioesters: Synthesis of Substituted Butenolides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Elusive Thiyl Radical Migration in a Visible Light Induced
Chemoselective Rearrangement of g-Keto Acrylate Thioesters:
Synthesis of Substituted Butenolides
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| Creator |
Naskar, Sandip
Das, Indrajit |
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| Subject |
Chemistry
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| 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.
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| Publisher |
John Wiley & Sons
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| Date |
2017-03-06
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| 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 |
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| Relation |
http://dx.doi.org/10.1002/adsc.201601016
http://www.eprints.iicb.res.in/2645/ |
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