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Issue 12, 2016
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Highly selective synthesis of 6-substituted benzothiophenes by Sc(OTf)3-catalyzed intermolecular cyclization and sulfur migration

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Abstract

A series of 6-substituted benzo[b]thiophenes was efficiently synthesized using a Sc(OTf)3-catalyzed intermolecular cyclization between para-substituted N-(arylthio)succinimides and alkynes taking advantage of a unique and selective 1,2-sulfur migration. Investigations with DFT shed light on the migration process occuring via an electrophilic ipso cyclization of a vinyl cation to a key spirocyclic thiete intermediate.

Graphical abstract: Highly selective synthesis of 6-substituted benzothiophenes by Sc(OTf)3-catalyzed intermolecular cyclization and sulfur migration

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Publication details

The article was received on 20 Aug 2016, accepted on 09 Sep 2016 and first published on 12 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00477F
Citation: Org. Chem. Front., 2016,3, 1619-1623
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    Highly selective synthesis of 6-substituted benzothiophenes by Sc(OTf)3-catalyzed intermolecular cyclization and sulfur migration

    X. Wang, T. Gensch and F. Glorius, Org. Chem. Front., 2016, 3, 1619
    DOI: 10.1039/C6QO00477F

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