Synthesis 2019; 51(17): 3313-3319
DOI: 10.1055/s-0037-1611787
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with DABSO and Phenyldiazonium Tetrafluoroborates for the Synthesis of 2-Sulfonylquinolines via a Radical Reaction

Guang-Hui Li
a  College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China   Email: [email protected]   Email: [email protected]
,
Dao-Qing Dong
a  College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China   Email: [email protected]   Email: [email protected]
,
Qi Deng
b  School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, P. R. of China
,
Shi-Qiang Yan
c  Shandong Dyne Marine Biopharmaceutical Co., Ltd., Weihai, Shandong 264300, P. R. of China
,
a  College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China   Email: [email protected]   Email: [email protected]
› Author Affiliations
We gratefully acknowledge the financial support from the National Natural Science Foundation of China (21402103, 21772107), the China Postdoctoral Science Foundation (150030), and the Research Fund of Qingdao Agricultural University’s Highlevel Person (631303).
Further Information

Publication History

Received: 14 February 2019

Accepted after revision: 14 March 2019

Publication Date:
15 May 2019 (online)


These authors contributed equally to this article.

Abstract

An efficient and practical method for the synthesis of 2-sulfonylquinolines through copper-catalyzed deoxygenative C2-sulfonylation of quinoline N-oxides with 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and phenyldiazonium tetrafluoroborates is demonstrated. Products with various substituents were obtained in moderate to high yields.

Supporting Information

 
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