Issue 34, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
06 Jul 2017
Accepted
09 Aug 2017
First published
09 Aug 2017

Org. Biomol. Chem., 2017,15, 7093-7096

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

J. Xu and P. Wipf, Org. Biomol. Chem., 2017, 15, 7093 DOI: 10.1039/C7OB01654A

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