Heterogeneously catalyzed domino synthesis of 3-indolylquinones involving direct oxidative C-C coupling of hydroquinones and indoles

TitleHeterogeneously catalyzed domino synthesis of 3-indolylquinones involving direct oxidative C-C coupling of hydroquinones and indoles
Publication TypeJournal Article
Year of Publication2017
AuthorsKamble, SB;, Vyas, PP, Jayaram, RV;, Rode, CV
JournalACS Omega
Volume2
Start Page2238-2247
Issue5
Date PublishedMAY
KeywordsCarbonyl compounds (organic); Electron microscopy; Fourier-transform spectroscopy; Redox reaction
Abstract
Abstract Image

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.

DOI10.1021/acsomega.7b00201
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

Not Available

Divison category: 
Chemical Engineering & Process Development