Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

Gregory Boyce; Stefania Musolino; Jianing Yang; Andrew Smith; James Taylor

doi:10.1021/acs.joc.2c01602

Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

Gregory Boyce, Stefania Musolino, Jianing Yang, Andrew Smith, James Taylor

Department of Chemistry

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

2 Citations (SciVal)

Abstract

The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.

Original language	English
Pages (from-to)	13367-13374
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	87
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.2c01602
Publication status	Published - 7 Oct 2022

Bibliographical note

Funding Information:
G.R.B. is grateful to Florida Gulf Coast University for a sabbatical award. The Engineering and Physical Sciences Research Council, University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) are thanked for financial support [Ph.D. studentship to S.F.M.; Grant Code: EP/L016419/1 and EP/J018139/1]. J.E.T. thanks the Leverhulme Trust (Grant Code: ECF-2014-005) and the EPSRC (Grant Code: EP/V051423/1).

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10.1021/acs.joc.2c01602Licence: CC BY

Cite this

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title = "Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols",

abstract = "The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Br{\o}nsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.",

author = "Gregory Boyce and Stefania Musolino and Jianing Yang and Andrew Smith and James Taylor",

note = "Funding Information: G.R.B. is grateful to Florida Gulf Coast University for a sabbatical award. The Engineering and Physical Sciences Research Council, University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) are thanked for financial support [Ph.D. studentship to S.F.M.; Grant Code: EP/L016419/1 and EP/J018139/1]. J.E.T. thanks the Leverhulme Trust (Grant Code: ECF-2014-005) and the EPSRC (Grant Code: EP/V051423/1). ",

year = "2022",

month = oct,

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doi = "10.1021/acs.joc.2c01602",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

AU - Boyce, Gregory

AU - Musolino, Stefania

AU - Yang, Jianing

AU - Smith, Andrew

AU - Taylor, James

N1 - Funding Information: G.R.B. is grateful to Florida Gulf Coast University for a sabbatical award. The Engineering and Physical Sciences Research Council, University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) are thanked for financial support [Ph.D. studentship to S.F.M.; Grant Code: EP/L016419/1 and EP/J018139/1]. J.E.T. thanks the Leverhulme Trust (Grant Code: ECF-2014-005) and the EPSRC (Grant Code: EP/V051423/1).

PY - 2022/10/7

Y1 - 2022/10/7

N2 - The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.

AB - The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.

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U2 - 10.1021/acs.joc.2c01602

DO - 10.1021/acs.joc.2c01602

M3 - Article

SN - 0022-3263

VL - 87

SP - 13367

EP - 13374

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

Abstract

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Boronic Acid-Catalysed Dehydrative Synthesis

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Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

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Bibliographical note

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Boronic Acid-Catalysed Dehydrative Synthesis

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