Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation

Susana Estopina-Duran, Liam Donnelly, Euan Mclean, Bryony Hockin, Alexandra M.Z. Slawin, James Taylor

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 arylboronic acid and oxalic acid.
Original languageEnglish
Pages (from-to)3950-3956
Number of pages7
JournalChemistry - A European Journal
Volume25
Issue number15
Early online date10 Jan 2019
DOIs
Publication statusPublished - 12 Mar 2019

Keywords

  • alcohols
  • boronic acids
  • etherification
  • homogeneous catalysis
  • substitution

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation. / Estopina-Duran, Susana; Donnelly, Liam; Mclean, Euan; Hockin, Bryony; Slawin, Alexandra M.Z.; Taylor, James.

In: Chemistry - A European Journal, Vol. 25, No. 15, 12.03.2019, p. 3950-3956.

Research output: Contribution to journalArticle

Estopina-Duran, Susana ; Donnelly, Liam ; Mclean, Euan ; Hockin, Bryony ; Slawin, Alexandra M.Z. ; Taylor, James. / Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 15. pp. 3950-3956.
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