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; Dao-Qing Dong; Qi Deng; Shi-Qiang Yan; Zu-Li Wang

doi:10.1055/s-0037-1611787

Synthesis, Table of Contents

Synthesis 2019; 51(17): 3313-3319
DOI: 10.1055/s-0037-1611787

paper

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

^aCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China Email: wangzulichem@163.com Email: wangzuli09@tsinghua.org.cn

,

Dao-Qing Dong

^aCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China Email: wangzulichem@163.com Email: wangzuli09@tsinghua.org.cn

,

Qi Deng

^bSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, P. R. of China

,

Shi-Qiang Yan

^cShandong Dyne Marine Biopharmaceutical Co., Ltd., Weihai, Shandong 264300, P. R. of China

,

Zu-Li Wang *

^aCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China Email: wangzulichem@163.com Email: wangzuli09@tsinghua.org.cn

› Author Affiliations

Abstract

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^◊ 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.

Key words

quinoline N-oxides - DABSO - radicals - sulfonylation - copper

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References

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