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Synlett 2018; 29(11): 1505-1509
DOI: 10.1055/s-0037-1609751
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© Georg Thieme Verlag Stuttgart · New York

Oxidative C–C Bond Cleavage for the Synthesis of Aryl Carboxylic Acids from Aryl Alkyl Ketones

Liang Xu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Shengpeng Wang
b   Transfar Zhilian Co., Ltd., Xiaoshan Economy & Technology Development Zone, Hangzhou 311215, P. R. of China
,
Bajin Chen
b   Transfar Zhilian Co., Ltd., Xiaoshan Economy & Technology Development Zone, Hangzhou 311215, P. R. of China
,
Meichao Li*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Xinquan Hu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Baoxiang Hu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Liqun Jin
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Nan Sun
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Zhenlu Shen*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
› Author Affiliations
This project was supported by the National Natural Science Foundation of China (21776260, 21773211 and 21376224), Natural Science Foundation of Zhejiang Province (LY17B060007) and Hangzhou ­Qianjiang Distinguished Experts Project.
Further Information

Publication History

Received: 05 March 2018

Accepted after revision: 11 April 2018

Publication Date:
16 May 2018 (online)

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Abstract

A metal-free and one-pot two-step synthesis of aryl carboxylic acids from aryl alkyl ketones has been achieved. The reactions were performed with iodine as the catalyst, DMSO and TBHP as the oxidants. Under the optimal reaction conditions, a number of aryl alkyl ketones could be converted into their corresponding aryl carboxylic acids in good to excellent yields (up to 94%).

Key words

aryl alkyl ketones - aryl carboxylic acids - iodine - dimethyl sulfoxide - tert-butyl hydroperoxide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609751.
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