Fast protodeboronation of arylboronic acids and esters with AlCl3 at room temperature
Zhijun Yuan A # , Yunshi Liang A # , Yiting He A , Huiying Deng A , Haiting Wu A , Bohong Lin A and Jing Zhang
A *
+ Author Affiliations
- Author Affiliations
A Artemisinin Research Center and The First Affiliated Hospital, Guangzhou University of Chinese Medicine, 12 Jichang Road, Guangzhou 510405, China.
* Correspondence to: jingzhang@gzucm.edu.cn
# These authors contributed equally to this paper
Handling Editor: Martyn Coles
Australian Journal of Chemistry 76(4) 194-200 https://doi.org/10.1071/CH23028
Submitted: 9 February 2023 Accepted: 25 May 2023 Published: 14 June 2023
© 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing.
Abstract
AlCl3-mediated protodeboronation of arylboronic acids and esters is reported herein. This method features mild reaction conditions, high reaction yields, as well as short reaction times. Mechanistic studies based on 11B NMR spectroscopy suggest that it might proceed through initial boron activation by coordination of AlCl3 to the oxygen atom of arylboronic acid or ester groups.
Keywords: 11B NMR spectroscopy, AlCl3, arylboronic acids, arylboronic esters, Brønsted acid, Lewis acid, mild reaction condition, protodeboronation.
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