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Heterogeneously Catalyzed Domino Synthesis of 3-Indolylquinones Involving Direct Oxidative C-C Coupling of Hydroquinones and Indoles.

ABSTRACT: A domino synthesis of 3-indolylquinones was achieved successfully via direct oxidative C-C coupling of hydroquinones with indoles over Ag₂O and Fe₃O₄/povidone-phosphotungstic acid (PVP-PWA) catalysts using H₂O₂ in tetrahydrofuran at room temperature. Ag₂O catalyzed the in situ oxidation of hydroquinone and 3-indolylhydroquinone intermediates, whereas ferrite solid acid, Fe₃O₄/PVP-PWA, with a 1:4:1 ratio of Fe₃O₄, PVP, and PWA, catalyzed the activation of quinones. The efficiency of this catalytic domino approach was established by a broad scope of substrates involving a variety of hydroquinones and quinones to give high yields (81-97%) of 3-indolylquinones. Fe₃O₄/PVP-PWA was separated magnetically, whereas simple filtration could separate Ag₂O, both of which could be recycled several times without losing their activities.

SUBMITTER: Kamble SB

PROVIDER: S-EPMC6640916 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Heterogeneously Catalyzed Domino Synthesis of 3-Indolylquinones Involving Direct Oxidative C-C Coupling of Hydroquinones and Indoles.

Kamble Sumit B SB Vyas Praneet P PP Jayaram Radha V RV Rode Chandrashekhar V CV

ACS omega 20170523 5

A domino synthesis of 3-indolylquinones was achieved successfully via direct oxidative C-C coupling of hydroquinones with indoles over Ag2O and Fe3O4/povidone-phosphotungstic acid (PVP-PWA) catalysts using H2O2 in tetrahydrofuran at room temperature. Ag2O catalyzed the in situ oxidation of hydroquinone and 3-indolylhydroquinone intermediates, whereas ferrite solid acid, Fe3O4/PVP-PWA, with a 1:4:1 ratio of Fe ...[more]

PMID: 31457575

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