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A copper-catalyzed three-component reaction of alkenes,cycloketone oximes and DABCO·(SO_(2))_(2):Direct C(sp^(2))-H cyanoalkylsulfonylation

A copper-catalyzed three-component reaction of alkenes, cycloketone oximes and DABCO·(SO2)2: Direct C(sp~2)-H cyanoalkylsulfonylation

作     者:Yating Liu Luoyu Wang Ling-Hui Zeng Yun Zhao Tonghao Zhu Jie Wu Yating Liu;Luoyu Wang;Ling-Hui Zeng;Yun Zhao;Tonghao Zhu;Jie Wu

作者机构:School of Pharmaceutical and Chemical Engineering&Institute for Advanced StudiesTaizhou UniversityTaizhou 318000China Department of PharmacologyZhejiang University City CollegeHangzhou 310015China State Key Laboratory of Organometallic ChemistryShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China School of Chemistry and Chemical EngineeringHenan Normal UniversityXinxiang 453007China 

出 版 物:《Chinese Chemical Letters》 (中国化学快报(英文版))

年 卷 期:2022年第33卷第5期

页      面:2383-2386页

核心收录:

学科分类:081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基  金:support from the National Natural Science Foundation of China (No. 21871053) the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang (No. 2019R01005) the Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University (No. 2020ZD04) is gratefully acknowledged 

主  题:Copper iodide Sulfur dioxide C-C bond cleavage C(sp^(2))-H Cyanoalkylsulfonylation Radical process 

摘      要:A copper-catalyzed three-component reaction of alkenes,cycloketone oximes and DABCO·(SO_(2))_(2) is de-veloped,which provides a convenient route for the synthesis of diverse(E)-cyanoalkylsulfonyl alkenes in moderate to good yields with excellent regio-and stereoselectivity.A broad substrate scope with ex-cellent functional group tolerance is observed.A plausible radical pathway is proposed,which involves copper-catalyzed ring-opening C–C bond cleavage of O-acyl oxime and insertion of sulfur *** the reaction process,cyanoalkyl radical and cyanoalkylsulfonyl radical are the key intermediates.

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