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Synthesis 2017; 49(18): 4350-4356
DOI: 10.1055/s-0036-1588487
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Arylation of Benzothiazoles with Toluene Derivatives­: Synthesis of 2-Arylbenzothiazole

Chengliang Li
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Hongmei Deng*
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China   Email: hmdeng@staff.shu.edu.cn
,
Tao Jin
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Zhiqiang Liu
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Ruolan Jiang
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Chunju Li
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Xueshun Jia*
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Jian Li*
c   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
› Author AffiliationsThe authors thank the National Natural Science Foundation of China (Nos: 21472121, 21272148) and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University for financial support.
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Publication History

Received: 22 April 2017

Accepted after revision: 05 June 2017

Publication Date:
25 July 2017 (online)

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Abstract

A copper-catalyzed reaction of benzothiazole and readily available toluene derivatives has been disclosed. This protocol is proposed to proceed through the oxidation of toluene and ring opening of benzothiazole, thus providing a new pathway for the synthesis of 2-arylbenzothiazoles.

Key words

toluene - oxidation - copper - benzothiazole - arylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588487.
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