Issue 32, 2015

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Abstract

A protocol has been developed for direct Csp3–Csp2 bond formation at the 4- and 6-positions of dibenzothiophenes using a gold(I) catalyst with terminal alkynes and dibenzothiophene-S-oxides. The sulfoxide acts as a traceless directing group to avoid the need to prefunctionalise at carbon. The iterative use of this protocol is possible and has been employed in the preparation of novel macrocyclic structures. In addition, a cascade process shows how oxyarylations can be combined with other processes resulting in complex, highly efficient transformations.

Graphical abstract: Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Supplementary files

Article information

Article type
Paper
Submitted
17 Jun 2015
Accepted
07 Jul 2015
First published
07 Jul 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 8676-8686

Author version available

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

M. J. Barrett, P. W. Davies and R. S. Grainger, Org. Biomol. Chem., 2015, 13, 8676 DOI: 10.1039/C5OB01241D

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