Iron-mediated oxidative C-H coupling of arenes and alkenes directed by sulfur: An expedient route to dihydrobenzofurans

Research output: Contribution to journalArticle

  • Authors:
  • Craig Cavanagh
  • Miles Aukland
  • Quentin Laurent
  • Alan Hennessy
  • David Procter

Abstract

A novel route to medicinally-relevant dihydrobenzofurans utilises a sulfur-directed C-H ortho-coupling of arenes and unactivated terminal alkenes mediated by iron, and a palladium-catalysed deallylation/heterocyclisation sequence. The iron-mediated coupling affords linear products of alkene chloroarylation in good yield and with complete regioselectivity. The coupling likely proceeds by redox-activation of the arene partner by iron(iii) and alkene addition to the resultant radical cation.

Bibliographical metadata

Original languageEnglish
Pages (from-to)5286-5292
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number23
Early online date11 May 2016
DOIs
StatePublished - 21 Jun 2016