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Indole synthesis by palladium-catalyzed tandem allylic isomerization – furan Diels–Alder reaction

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Abstract

A Pd(0)-catalyzed elimination of an allylic acetate generates a π-allyl complex that is postulated to initiate a novel intramolecular Diels–Alder cycloaddition to a tethered furan (IMDAF). Under the reaction conditions, this convergent, microwave-accelerated cascade process provides substituted indoles in moderate to good yields after Pd-hydride elimination, aromatization by dehydration, and in situ N-Boc cleavage.

Graphical abstract: Indole synthesis by palladium-catalyzed tandem allylic isomerization – furan Diels–Alder reaction

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Publication details

The article was received on 06 Jul 2017, accepted on 09 Aug 2017 and first published on 09 Aug 2017


Article type: Communication
DOI: 10.1039/C7OB01654A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Indole synthesis by palladium-catalyzed tandem allylic isomerization – furan Diels–Alder reaction

    J. Xu and P. Wipf, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01654A

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