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Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions
Guo, Tenglong1; Jiang, Quanbin1; Yu, Zhengkun1,2
KeywordC-h Functionalization Copper Enamines Internal Olefins Thiolactones
Source PublicationADVANCED SYNTHESIS & CATALYSIS
2016-11-03
DOI10.1002/adsc.201600675
Volume358Issue:21Pages:3450-3457
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Applied ; Chemistry, Organic
WOS Research AreaChemistry
WOS KeywordAZIDE-ALKYNE CYCLOADDITION ; METAL-FREE ; UNACTIVATED ALKENES ; FORMING REACTIONS ; MOLECULAR-OXYGEN ; FACILE SYNTHESIS ; PRIMARY AMINES ; ACTIVATION ; DITHIOACETALS ; AMINATION
AbstractA copper(I)-catalyzed, (diacetoxyiodo)benzene [PhI(OAc)(2)]-mediated ring-expansion/thiolactonization of alpha-oxo ketene dithioacetals was efficiently realized via azidation of the internal olefinic C-H bond with sodium azide under mild conditions. Sequential amination, ring-expansion rearrangement, and thiolactonization occurred to form aminated thiolactones in the presence of acetic anhydride as the additive, while only C-H amination to afford the unprotected enamines occurred when using ammonium sulfide as a reducing additive. The in situ generated vinyl azides were confirmed as the reactive intermediates, which were captured by phenylacetylene to produce triazoles. This protocol provides a concise route to thiolactone derivatives and unprotected enamines.
Language英语
WOS IDWOS:000390407300015
Citation statistics
Cited Times:6[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/150506
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, Liaoning, Peoples R China
2.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
Guo, Tenglong,Jiang, Quanbin,Yu, Zhengkun. Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions[J]. ADVANCED SYNTHESIS & CATALYSIS,2016,358(21):3450-3457.
APA Guo, Tenglong,Jiang, Quanbin,&Yu, Zhengkun.(2016).Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions.ADVANCED SYNTHESIS & CATALYSIS,358(21),3450-3457.
MLA Guo, Tenglong,et al."Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions".ADVANCED SYNTHESIS & CATALYSIS 358.21(2016):3450-3457.
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