Issue 3, 2018
From the journal:

Organic Chemistry Frontiers

A copper-catalyzed sulfonylative C–H bond functionalization from sulfur dioxide and aryldiazonium tetrafluoroborates†

Hongguang Xia,*a   Yuanyuan An,b   Xincheng Zenga  and  Jie Wu ORCID logo *bc  

* Corresponding authors

a Department of Biochemistry and Molecular Biology, Zhejiang University School of Medicine, Hangzhou 310058, China
E-mail: hongguangxia@zju.edu.cn

b Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China
E-mail: jie_wu@fudan.edu.cn

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

Abstract

Sulfonylative C–H bond functionalization through a copper-catalyzed three-component reaction of 8-aminoquinoline amides, DABCO·(SO2)2 and aryldiazonium tetrafluoroborates is developed. Excellent selectivity in the para-position is observed for this copper-catalyzed transformation. This reaction is triggered by a copper-chelated complex via the coordination of the copper catalyst with the substrate and arylsulfonyl radical generated in situ, thus providing 5-sulfonyl-8-aminoquinoline amides in moderate to good yields.

Graphical abstract: A copper-catalyzed sulfonylative C–H bond functionalization from sulfur dioxide and aryldiazonium tetrafluoroborates

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Article information

DOI
https://doi.org/10.1039/C7QO00866J
Article type
Research Article
Submitted
23 Sept. 2017
Accepted
03 Okt. 2017
First published
11 Okt. 2017

Org. Chem. Front., 2018,5, 366-370

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A copper-catalyzed sulfonylative C–H bond functionalization from sulfur dioxide and aryldiazonium tetrafluoroborates

H. Xia, Y. An, X. Zeng and J. Wu, Org. Chem. Front., 2018, 5, 366 DOI: 10.1039/C7QO00866J

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