Gold-Catalysed Oxyarylation of Styrenes and Mono- and gem-Disubstituted Olefins Facilitated by an Iodine(III) Oxidant

Liam T. Ball, Guy C. Lloyd-Jones*, Christopher A. Russell

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

1-Hydroxy-1,2-benziodoxol-3(1H)-one (IBA) is an efficient terminal oxidant for gold-catalysed, three-component oxyarylation reactions. The use of this iodine(III) reagent expands the scope of oxyarylation to include styrenes and gem-disubstituted olefins, substrates that are incompatible with the previously reported Selectfluor-based methodology. Diverse arylsilane coupling partners can be employed, and in benzotrifluoride, homocoupling is substantially reduced. In addition, the IBA-derived co-products can be recovered and recycled.

Original languageEnglish
Pages (from-to)2931-2937
Number of pages7
JournalChemistry - A European Journal
Volume18
Issue number10
DOIs
Publication statusPublished - Mar 2012

Keywords

  • arylation
  • gold
  • homogeneous catalysis
  • hypervalent iodine
  • styrenes
  • SELECTFLUOR(TM) REAGENT F-TEDA-BF4
  • CROSS-COUPLING REACTIONS
  • ORGANOGOLD COMPOUNDS
  • FLUORINATING AGENTS
  • DIRECT ALKYNYLATION
  • ARYL IODIDES
  • ALKENES
  • OXIDATION
  • ACIDS
  • BIS(TETRAFLUOROBORATE)

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