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

	Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles
	Mao, Zhifeng 1; Huang, Fei 1; Yu, Haifeng 2; Chen, Jiping 1; Yu, Zhengkun 1,3; Xu, Zhaoqing 4
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
通讯作者	余正坤
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	物理化学
WOS标题词	science & technology ; physical sciences
类目[WOS]	chemistry, multidisciplinary
研究领域[WOS]	chemistry
关键词[WOS]	silver-mediated trifluoromethylation ; pd(ii)-catalyzed ortho-trifluoromethylation ; hypervalent iodine reagent ; light photoredox catalysis ; oxo ketene dithioacetals ; oxidative trifluoromethylation ; room-temperature ; unactivated olefins ; terminal alkenes ; arenes
收录类别	SCI ; IC ; CCR
语种	英语
WOS记录号	WOS:000332747400026
公开日期	2016-05-09
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/144092]
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, Dalian 116023, Peoples R China 2.Anshan Normal Univ, Dept Chem, Anshan 114007, Liaoning, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China 4.Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China
推荐引用方式 GB/T 7714	Mao, Zhifeng,Huang, Fei,Yu, Haifeng,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, Zhifeng,Huang, Fei,Yu, Haifeng,Chen, Jiping,Yu, Zhengkun,&Xu, Zhaoqing.(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, Zhifeng,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.