Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles

doi:10.1002/chem.201305069

CORC > 兰州大学 > 兰州大学 > 基础医学院 > 期刊论文

	Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles
	Mao, ZF; Huang, F; Yu, HF; Chen, JP; Yu, ZK; Xu, ZQ; Yu, ZK (reprint author), Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China.
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2014-03-17
卷号	20 期号:12 页码:3439-3445
关键词	CH activation copper olefins trifluoromethylation
ISSN号	0947-6539
DOI	10.1002/chem.201305069
文献子类	Article
英文摘要	The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient Cu-II-catalyzed trifluoromethylation of internal olefins, that is, -oxoketene dithioacetals, has been achieved by using Cu(OH)(2) as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic CH trifluoromethylation. Cyclic and acyclic dithioalkyl -oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic CH bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.
学科主题	Chemistry
出版地	WEINHEIM
资助项目	国家自然科学基金项目
项目编号	National Natural Science Foundation of China [21272232, 21102141]
语种	英语
WOS记录号	WOS:000332747400026
资助机构	NSFC
内容类型	期刊论文
源URL	[http://ir.lzu.edu.cn/handle/262010/121686]
专题	基础医学院_期刊论文
通讯作者	Yu, ZK (reprint author), Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China.
推荐引用方式 GB/T 7714	Mao, ZF,Huang, F,Yu, HF,et al. Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles[J]. CHEMISTRY-A EUROPEAN JOURNAL,2014,20(12):3439-3445.
APA	Mao, ZF.,Huang, F.,Yu, HF.,Chen, JP.,Yu, ZK.,...&Yu, ZK .(2014).Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles.CHEMISTRY-A EUROPEAN JOURNAL,20(12),3439-3445.
MLA	Mao, ZF,et al."Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles".CHEMISTRY-A EUROPEAN JOURNAL 20.12(2014):3439-3445.