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学科主题: 物理化学
题名: Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles
作者: Mao, Zhifeng1;  Huang, Fei1;  Yu, Haifeng2;  Chen, Jiping1;  Yu, Zhengkun1, 3;  Xu, Zhaoqing4
通讯作者: 余正坤
关键词: CH activation ;  copper ;  olefins ;  trifluoromethylation
刊名: CHEMISTRY-A EUROPEAN JOURNAL
发表日期: 2014-03-17
DOI: 10.1002/chem.201305069
卷: 20, 期:12, 页:3439-3445
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
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.
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
语种: 英语
WOS记录号: WOS:000332747400026
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/144092
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, 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

Recommended Citation:
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.
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