Aryl boronic acid catalysed dehydrative substitution of benzylic alcohols for C−O bond formation
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: https://orcid.org/0000-0003-3342-4902, Mclean, Euan B., Hockin, Bryony M., Slawin, Alexandra M. Z. and Taylor, James E.;
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Item type: Article ID code: 83383 Dates: DateEvent12 March 2019Published10 January 2019AcceptedNotes: 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: 11 Nov 2024 13:41 URI: https://strathprints.strath.ac.uk/id/eprint/83383
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