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

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

Research output: Contribution to journal › Article › peer-review

51 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 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

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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.",

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

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doi = "10.1002/chem.201806057",

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T1 - Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation

AU - Estopiñá-Durán, Susana

AU - Donnelly, Liam

AU - Mclean, Euan B.

AU - Hockin, Bryony M.

AU - Slawin, Alexandra M. Z.

AU - Taylor, James E.

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.

U2 - 10.1002/chem.201806057

DO - 10.1002/chem.201806057

M3 - Article

SN - 0947-6539

VL - 25

SP - 3950

EP - 3956

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 15

ER -

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

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