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

doi:10.1002/chem.201806057

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

Pure And Applied Chemistry

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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.

Original language	English
Pages (from-to)	3950-3956
Number of pages	7
Journal	Chemistry - A European Journal
Volume	25
Issue number	15
DOIs	https://doi.org/10.1002/chem.201806057
Publication status	Published - 12 Mar 2019

Keywords

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

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10.1002/chem.201806057

Estopina-Duran-etal-CEJ2019-Aryl-boronic-acid-catalysed-dehydrative-substitution-benzylic-alcohols-C−O-bond-formationAccepted author manuscript, 1.7 MB

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title = "Aryl boronic acid catalysed dehydrative substitution of benzylic alcohols for C−O bond formation",

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.",

keywords = "alcohols, boronic acids, etherification, homogeneous catalysis, substitution, pentafluorophenylboronic acid, oxalic acid, intermolecular substitution, intramolecular cyclisations",

author = "Susana Estopi{\~n}{\'a}-Dur{\'a}n and Donnelly, {Liam J,} and Mclean, {Euan B.} and Hockin, {Bryony M.} and Slawin, {Alexandra M. Z.} and Taylor, {James E.}",

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TY - JOUR

T1 - Aryl boronic acid catalysed dehydrative substitution of benzylic alcohols for C−O bond formation

AU - Estopiñá-Durán, Susana

AU - Donnelly, Liam J,

AU - Mclean, Euan B.

AU - Hockin, Bryony M.

AU - Slawin, Alexandra M. Z.

AU - Taylor, James E.

N1 - Chem. Eur. J. 10.1002/chem.201806057

PY - 2019/3/12

Y1 - 2019/3/12

N2 - 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.

AB - 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.

KW - alcohols

KW - boronic acids

KW - etherification

KW - homogeneous catalysis

KW - substitution

KW - pentafluorophenylboronic acid

KW - oxalic acid

KW - intermolecular substitution

KW - intramolecular cyclisations

U2 - 10.1002/chem.201806057

DO - 10.1002/chem.201806057

M3 - Article

VL - 25

SP - 3950

EP - 3956

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 15

ER -

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

Abstract

Keywords

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