Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Paul Davies; Richard Grainger; Matthew Barrett

doi:10.1039/C5OB01241D

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Paul Davies, Richard Grainger, Matthew Barrett

Chemistry

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17 Citations (Scopus)

190 Downloads (Pure)

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.

Original language	English
Pages (from-to)	8676-8686
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	32
Early online date	7 Jul 2015
DOIs	https://doi.org/10.1039/C5OB01241D
Publication status	Published - 28 Aug 2015

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10.1039/C5OB01241D

Barrett_et_al_Regioselective_functionalisation_Organic_Biomolecular_Chemistry_2015
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17 Citations
2 Article

Gold-catalyzed intermolecular alkyne oxyarylation for C3-functionalization of benzothiophenes
Rist, P., Grainger, R. & Davies, P., 5 Feb 2021, In: Organic Letters. 23, 3, p. 642–646 5 p.
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Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation
Barrett, M., Khan, G., Davies, P. & Grainger, R., 25 May 2017, In: Chemical Communications . 53, 42, p. 5733-5736 4 p.
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Open Access
File
20 Citations (Scopus)

192 Downloads (Pure)

Birmingham Environment for Academic Research (BEAR)
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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.",

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Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Abstract

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Research output

Gold-catalyzed intermolecular alkyne oxyarylation for C3-functionalization of benzothiophenes

Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation

Equipment

Birmingham Environment for Academic Research (BEAR)

Cite this