Issue 93, 2019
From the journal:

Chemical Communications

Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics†

Melanie A. Drew, ORCID logo a   Sebastian Arndt,b   Christopher Richardson, ORCID logo a   Matthias Rudolph,b   A. Stephen K. Hashmi ORCID logo *b  and  Christopher J. T. Hyland ORCID logo *a  

* Corresponding authors

a School of Chemistry and Molecular Bioscience, and Molecular Horizons Research Institute, University of Wollongong, Northfields Avenue, Wollongong, Australia
E-mail: chris_hyland@uow.edu.au

b Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, Heidelberg, Germany

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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Article information

DOI
https://doi.org/10.1039/C9CC06241F
Article type
Communication
Submitted
14 Aug 2019
Accepted
11 Oct 2019
First published
15 Oct 2019

Chem. Commun., 2019,55, 13971-13974

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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, 55, 13971 DOI: 10.1039/C9CC06241F

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