4.6 Article

Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 20, Pages 3898-3902

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00702a

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Funding

  1. Takeda Science Foundation

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3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (Nb2O5/C) and palladium-on-carbon (Pd/C) under heating conditions without any oxidants. The Lewis acidic Nb2O5/C promoted the nucleophilic addition of indoles to the cyclohexanones, and the subsequent dehydration and Pd/C-catalyzed dehydrogenation produced the 3-arylindoles. The additive 2,3-dimethyl-1,3-butadiene worked as a hydrogen acceptor to facilitate the dehydrogenation step.

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