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Issue 32, 2015
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Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

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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

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Publication details

The article was received on 17 Jun 2015, accepted on 07 Jul 2015 and first published on 07 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01241D
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Citation: Org. Biomol. Chem., 2015,13, 8676-8686
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    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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