Chinese Journal of Organic Chemistry >
Copper-Catalyzedortho-Sulfonylation with 5-Chloro-8-aminoquinoline Group-Directed
Received date: 2020-05-09
Revised date: 2020-07-28
Online published: 2020-08-06
Supported by
the National Natural Science Foundation of China(21772222); the National Natural Science Foundation of China(21821002); the Department of Education of Guangdong Province(2017KSYS010); the Department of Education of Guangdong Province(2017KZDXM084); the Department of Education of Guangdong Province(2019KZDZX2003); the Department of Education of Guangdong Province(2019KZDXM035)
Sulfone is a common structure in natural products and active molecules, and also an important intermediate in organic synthesis. Sulfonylation is one of the most basic and important reactions in organic synthesis. The direct sulfonylation of C(sp 2)—H bond has been successfully realized by copper catalysis using 5-chloro-8-aminoquinoline (AQ') as a bidentate guiding group and various substituted sodium arylsulfites as sulfonylation reagent. This reaction has high functional group tolerance and a wide scope of substrates, including substrates with double substituents or fused rings. AQ' bidentate guiding group can be removed easily, which provides a new method for the synthesis of sulfone compounds. The reaction could be scaled up to the gram scale with a good yield.
Xiangyang Wang , Junqing Gao , Xuetao Xu , Ping Fang , Tiansheng Mei . Copper-Catalyzedortho-Sulfonylation with 5-Chloro-8-aminoquinoline Group-Directed[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 384 -393 . DOI: 10.6023/cjoc202005021
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