DICP OpenIR
Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones
He, Yuan1,2; Lou, Jiang1,2; Wu, Kaikai1; Wang, Hongmei3; Yu, Zhengkun1,4
Corresponding AuthorWang, Hongmei(wanghongmei@dicp.ac.cn) ; Yu, Zhengkun(zkyu@dicp.ac.cn)
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
2019-02-15
ISSN0022-3263
DOI10.1021/acs.joc.8b03175
Volume84Issue:4Pages:2178-2190
Funding ProjectNational Natural Science Foundation of China[21871253] ; National Natural Science Foundation of China[21472185] ; National Basic Research Program of China[2015CB856600]
Funding OrganizationNational 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
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordCYCLOBUTANONE O-BENZOYLOXIMES ; KETENE N,S-ACETALS ; IMINYL RADICALS ; THIOBENZOYLKETENE S,N-ACETALS ; THIOAROYLKETENE S,N-ACETALS ; H CYANOALKYLATION ; N-TOSYLHYDRAZONES ; RING-CLEAVAGE ; REAGENTS ; ACCESS
AbstractCarbon-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.
Language英语
Funding OrganizationNational 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
WOS IDWOS:000459367100050
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/165807
Collection中国科学院大连化学物理研究所
Corresponding AuthorWang, Hongmei; Yu, Zhengkun
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.State Key Lab NBC Protect Civilian, Beijing 102205, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
Recommended Citation
GB/T 7714
He, Yuan,Lou, Jiang,Wu, Kaikai,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 He, Yuan,Lou, Jiang,Wu, Kaikai,Wang, Hongmei,&Yu, Zhengkun.(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 He, Yuan,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.
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