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A regioselective one-pot aza-Friedel–Crafts reaction for primary, secondary and tertiary anilines using a heterogeneous catalyst

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Abstract

A one-pot multicomponent aza-Friedel–Crafts reaction was performed under green, neat and heterogeneous conditions in the presence of 1.25 mmol% of 30% w/w silicotungstic acid supported on Amberlyst 15 beads. In a yet unprecedented attempt, both primary and secondary anilines could provide the 3-substituted indole product in good to excellent yields usually at room temperature whilst tertiary anilines gave moderate results. Interestingly all reactions proceeded regioselectively via two separate C–C bond forming reactions rather than C–C and C–N bond forming steps. The catalyst is easy, safe and environmentally-benign to prepare, completely recoverable and recyclable up to 5 times.

Graphical abstract: A regioselective one-pot aza-Friedel–Crafts reaction for primary, secondary and tertiary anilines using a heterogeneous catalyst

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Publication details

The article was received on 06 Jul 2017, accepted on 23 Oct 2017 and first published on 23 Oct 2017


Article type: Paper
DOI: 10.1039/C7GC02038D
Citation: Green Chem., 2017, Advance Article
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    A regioselective one-pot aza-Friedel–Crafts reaction for primary, secondary and tertiary anilines using a heterogeneous catalyst

    G. Bosica and R. Abdilla, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC02038D

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