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题名: Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions
作者: Guo, Tenglong1;  Jiang, Quanbin1;  Yu, Zhengkun1, 2
关键词: C-H functionalization ;  copper ;  enamines ;  internal olefins ;  thiolactones
刊名: ADVANCED SYNTHESIS & CATALYSIS
发表日期: 2016-11-03
DOI: 10.1002/adsc.201600675
卷: 358, 期:21, 页:3450-3457
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Applied ;  Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: A 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.
关键词[WOS]: AZIDE-ALKYNE CYCLOADDITION ;  METAL-FREE ;  UNACTIVATED ALKENES ;  FORMING REACTIONS ;  MOLECULAR-OXYGEN ;  FACILE SYNTHESIS ;  PRIMARY AMINES ;  ACTIVATION ;  DITHIOACETALS ;  AMINATION
语种: 英语
WOS记录号: WOS:000390407300015
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/150506
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.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:
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.
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