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Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

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Abstract

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel–Crafts mechanism.

Graphical abstract: Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

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Publication details

The article was received on 14 Aug 2019, accepted on 11 Oct 2019 and first published on 15 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06241F
Chem. Commun., 2019, Advance Article

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    Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

    M. A. Drew, S. Arndt, C. Richardson, M. Rudolph, A. S. K. Hashmi and C. J. T. Hyland, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06241F

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