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

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Estopiñá-Durán, Susana and Donnelly, Liam J, and Mclean, Euan B. and Hockin, Bryony M. and Slawin, Alexandra M. Z. and Taylor, James E. (2019) Aryl boronic acid catalysed dehydrative substitution of benzylic alcohols for C−O bond formation. Chemistry - A European Journal, 25 (15). pp. 3950-3956. ISSN 1521-3765 (https://doi.org/10.1002/chem.201806057)

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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.

ORCID iDs

Estopiñá-Durán, Susana, Donnelly, Liam J, ORCID logoORCID: https://orcid.org/0000-0003-3342-4902, Mclean, Euan B., Hockin, Bryony M., Slawin, Alexandra M. Z. and Taylor, James E.;
  • Item type:Article
    ID code:83383
    Dates:
    Date
    Event
    12 March 2019
    Published
    10 January 2019
    Accepted
    Notes:Chem. Eur. J. 10.1002/chem.201806057
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:01 Dec 2022 11:40
    Last modified:03 Dec 2024 01:24
    URI:https://strathprints.strath.ac.uk/id/eprint/83383
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