Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols

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.

Citation

Boyce , G , Musolino , S F , Yang , J , Smith , A D & Taylor , J 2022 , ' Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols ' , The Journal of Organic Chemistry , vol. 87 , no. 19 , pp. 13367-13374 . https://doi.org/10.1021/acs.joc.2c01602

Publication

The Journal of Organic Chemistry

Status

Peer reviewed

DOI

https://doi.org/10.1021/acs.joc.2c01602

ISSN

0022-3263

Type

Journal article

Rights

Copyright © 2022 The Authors. Published by American Chemical Society. Open Access. This article is distributed under the terms of the Creative Commons Attribution 4.0 License (https://creativecommons.org/licenses/by/4.0/) which permits any use, reproduction and distribution of the work without further permission provided the original work is attributed

Description

Funding: Florida Gulf Coast University; University of St Andrews; UK Engineering and Physical Sciences Research Council - EP/J018139/1, EP/L016419/1, EP/V051423/1; Leverhulme Trust - ECF-2014-005.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/25982