Aryl boronic acid catalysed dehydrative substitution of benzylic alcohols for C−O bond formation

Susana Estopiñá-Durán, Liam J, Donnelly, Euan B. Mclean, Bryony M. Hockin, Alexandra M. Z. Slawin, James E. Taylor

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)
29 Downloads (Pure)

Abstract

A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C−O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
Original languageEnglish
Pages (from-to)3950-3956
Number of pages7
JournalChemistry - A European Journal
Volume25
Issue number15
DOIs
Publication statusPublished - 12 Mar 2019

Keywords

  • alcohols
  • boronic acids
  • etherification
  • homogeneous catalysis
  • substitution
  • pentafluorophenylboronic acid
  • oxalic acid
  • intermolecular substitution
  • intramolecular cyclisations

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