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Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives
Huang, Fei1,2; Liu, Zhuqing1,2; Wang, Quannan1,2; Lou, Jiang1,2; Yu, Zhengkun1,3
Source PublicationORGANIC LETTERS
2017-07-07
DOI10.1021/acs.orglett.7b01668
Volume19Issue:13Pages:3660-3663
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordC-C BOND ; DIAZO-COMPOUNDS ; ENANTIOSELECTIVE INSERTION ; KETENE N,S-ACETALS ; H BONDS ; FUNCTIONALIZATION ; ACTIVATION ; CARBON ; DIAZOESTERS ; TRANSFORMATIONS
AbstractEfficient copper-catalyzed formal carbene migratory insertion into the olefinic C=C bonds of internal olefins, that is, alpha-oxo ketene N,S-acetals, has been achieved by means of N-tosylhydrazones of ketones as the carbene precursors. Iminofuran derivatives were obtained and further transformed to the corresponding 2(3H)-furanones and 4-oxobutanoates (gamma-ketoesters), respectively, under mild conditions. In a similar fashion, alpha-thioxo ketene N,S-acetals reacted with N-tosylhydrazones of ketones to afford iminothiophenes. It is suggested that formal carbene migratory insertion into the olefinic C=C bond is involved in the overall catalytic cycle, demonstrating a new type of carbene insertion reaction for five-membered heterocycle construction.
Language英语
WOS IDWOS:000405358300083
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/152043
Collection中国科学院大连化学物理研究所
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.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
Huang, Fei,Liu, Zhuqing,Wang, Quannan,et al. Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives[J]. ORGANIC LETTERS,2017,19(13):3660-3663.
APA Huang, Fei,Liu, Zhuqing,Wang, Quannan,Lou, Jiang,&Yu, Zhengkun.(2017).Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives.ORGANIC LETTERS,19(13),3660-3663.
MLA Huang, Fei,et al."Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives".ORGANIC LETTERS 19.13(2017):3660-3663.
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