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

Research output: Contribution to journalArticle

DOI

Open Access Status

  • Embargoed (until 11/02/20)

Author(s)

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

School/Research organisations

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.
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Details

Original languageEnglish
JournalChemistry - A European Journal
VolumeEarly View
Early online date11 Feb 2019
DOIs
Publication statusE-pub ahead of print - 11 Feb 2019

    Research areas

  • Alcohols, Homogeneous catalysis, Boronic acids, Etherification, Substitution

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