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

Sumit B. Kamble | Zendy; Praneet P. Vyas | Zendy; Radha V. Jayaram | Zendy; Chandrashekhar V. Rode | Zendy

Open Access

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

Author(s) -

Sumit B. Kamble,

Praneet P. Vyas,

Radha V. Jayaram,

Chandrashekhar V. Rode

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00201

Subject(s) - catalysis , phosphotungstic acid , domino , chemistry , hydroquinone , oxidative coupling of methane , ferric , oxidative phosphorylation , combinatorial chemistry , organic chemistry , photochemistry , biochemistry

A domino synthesis of 3-indolylquinones was achieved successfully via direct oxidative C-C coupling of hydroquinones with indoles over Ag 2 O and Fe 3 O 4 /povidone-phosphotungstic acid (PVP-PWA) catalysts using H 2 O 2 in tetrahydrofuran at room temperature. Ag 2 O catalyzed the in situ oxidation of hydroquinone and 3-indolylhydroquinone intermediates, whereas ferrite solid acid, Fe 3 O 4 /PVP-PWA, with a 1:4:1 ratio of Fe 3 O 4 , 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. Fe 3 O 4 /PVP-PWA was separated magnetically, whereas simple filtration could separate Ag 2 O, both of which could be recycled several times without losing their activities.

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