Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions

	Copper-Catalyzed Ring-Expansion/Thiolactonization via Azidation of Internal Olefinic C-H Bond under Mild Conditions
	Guo, Tenglong 1; Jiang, Quanbin 1; Yu, Zhengkun 1,2
刊名	ADVANCED SYNTHESIS & CATALYSIS
	2016-11-03
卷号	358 期号:21 页码:3450-3457
关键词	C-H functionalization copper enamines internal olefins thiolactones
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.
WOS标题词	Science & Technology ; Physical Sciences
类目[WOS]	Chemistry, Applied ; Chemistry, Organic
研究领域[WOS]	Chemistry
关键词[WOS]	AZIDE-ALKYNE CYCLOADDITION ; METAL-FREE ; UNACTIVATED ALKENES ; FORMING REACTIONS ; MOLECULAR-OXYGEN ; FACILE SYNTHESIS ; PRIMARY AMINES ; ACTIVATION ; DITHIOACETALS ; AMINATION
收录类别	SCI
语种	英语
WOS记录号	WOS:000390407300015
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/150506]
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
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
推荐引用方式 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.