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Issue 19, 2012
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Unprecedented dithiolation of enals via their NHC-catalysed umpolung reaction with organic disulfides

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Abstract

A novel one-pot N-heterocyclic carbene (NHC)-catalysed dithiolation of α,β-unsaturated aldehydes (enals) with organic disulfides is reported. The protocol involves homoenolate reactivity of enals, where the homoenolate attacks on the disulfide as a d3 nucleophile followed by thioesterification to afford β-aryl/alkylsulfanyl thioesters with complete atom economy.

Graphical abstract: Unprecedented dithiolation of enals via their NHC-catalysed umpolung reaction with organic disulfides

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Publication details

The article was received on 01 Feb 2012, accepted on 08 Mar 2012, published on 09 Mar 2012 and first published online on 09 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25238D
Citation: Org. Biomol. Chem., 2012,10, 3932-3936
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    Unprecedented dithiolation of enals via their NHC-catalysed umpolung reaction with organic disulfides

    S. Singh and L. D. S. Yadav, Org. Biomol. Chem., 2012, 10, 3932
    DOI: 10.1039/C2OB25238D

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