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Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones

文献类型：期刊论文

作者Yu, Zhengkun2,4; Wang, Hongmei1; He, Yuan2,3; Lou, Jiang2,3; Wu, Kaikai2
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2019-02-15
卷号84期号:4页码:2178-2190
ISSN号0022-3263
DOI10.1021/acs.joc.8b03175
通讯作者Wang, Hongmei(wanghongmei@dicp.ac.cn) ; Yu, Zhengkun(zkyu@dicp.ac.cn)
英文摘要Carbon-carbon bond formation is among the most important reactions in organic synthesis. Reconstruction of a carbon-carbon bond through ring-opening C-C bond cleavage of a strained carbocycle usually occurs via a thermodynamically preferable pathway. However, carbon-carbon bond formation through thermodynamically less favorable C-C bond cleavage has seldom been documented. Herein, we disclose an unusual C-C bond cleavage of cycloketone oxime esters for [4+1] annulation. Under anaerobic copper(I) catalysis, cycloketone oxime esters underwent regioselective, thermodynamically less favorable radical C-C bond cleavage followed by annulation with enaminothiones; that is, alpha-thioxo ketene N,S-acetals efficiently affording 2-cyanoalkylaminothiophene derivatives. Cyclobutanone, -pentanone, -hexanone, and -heptanone oxime esters could act as the effective Cl building blocks in the annulation reaction. An iminyl radical mechanism is proposed for the rare C-C bond cleavage/[4+1] annulation cascade.
WOS关键词CYCLOBUTANONE O-BENZOYLOXIMES ; KETENE N,S-ACETALS ; IMINYL RADICALS ; THIOBENZOYLKETENE S,N-ACETALS ; THIOAROYLKETENE S,N-ACETALS ; H CYANOALKYLATION ; N-TOSYLHYDRAZONES ; RING-CLEAVAGE ; REAGENTS ; ACCESS
资助项目National Natural Science Foundation of China[21871253] ; National Natural Science Foundation of China[21472185] ; National Basic Research Program of China[2015CB856600]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000459367100050
出版者AMER CHEMICAL SOC
资助机构National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China
源URL[http://cas-ir.dicp.ac.cn/handle/321008/165806]  
专题大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者Yu, Zhengkun; Wang, Hongmei
作者单位1.State Key Lab NBC Protect Civilian, Beijing 102205, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
推荐引用方式
GB/T 7714		 Yu, Zhengkun,Wang, Hongmei,He, Yuan,et al. Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones[J]. JOURNAL OF ORGANIC CHEMISTRY,2019,84(4):2178-2190.
APA Yu, Zhengkun,Wang, Hongmei,He, Yuan,Lou, Jiang,&Wu, Kaikai.(2019).Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones.JOURNAL OF ORGANIC CHEMISTRY,84(4),2178-2190.
MLA Yu, Zhengkun,et al."Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones".JOURNAL OF ORGANIC CHEMISTRY 84.4(2019):2178-2190.

入库方式： OAI收割

来源：大连化学物理研究所

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