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

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Abstract

C3-selective C-C bond formation on benzothiophenes is challenging, and few direct functionalization methods are available. A gold-catalyzed reaction of alkynes with benzothiophene S-oxides provides regioselective entry into C3-alkylated benzothiophenes with the C7-alkylated isomer as the minor product. This oxyarylation reaction works with alkyl and aryl alkynes and substituted and unsubstituted benzothiophenes. Mechanistic studies identify that sulfoxide inhibits the catalyst [DTBPAu(PhCN)]SbF6, which also degrades and forms the unreactive complex [(DTBP)2Au]SbF6.

Original languageEnglish
Pages (from-to)642–646
Number of pages5
JournalOrganic Letters
Volume23
Issue number3
Early online date19 Jan 2021
DOIs
Publication statusPublished - 5 Feb 2021

Bibliographical note

Funding Information:
We thank the EPSRC for a studentship to P.A.R. (EP/N509590/1). The authors gratefully acknowledge support from the Centre for Chemical and Materials Analysis in the School of Chemistry and Dr. Cécile le Duff for NMR support. P.W.D. is grateful to the Royal Society and the Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033).

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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