Copper-catalyzed gem-difluoromethylenation of C(sp2)-H bonds of alkenes

被引：19
|
作者：
Xu, Hui [1 ]
Wang, Dejing [1 ]
Chen, Yunrong [1 ]
Wan, Wen [1 ]
Deng, Hongmei [2 ]
Ma, Kesen [3 ]
Wu, Shaoxiong [4 ]
Hao, Jian [1 ,5 ]
Jiang, Haizhen [1 ,5 ]
机构：
[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China
[2] Shanghai Univ, Lab Microstruct, Shanghai 200444, Peoples R China
[3] Univ Waterloo, Dept Biol, 200 Univ Ave West, Waterloo, ON N2L 3G1, Canada
[4] Emory Univ, Emory NMR Res Ctr, 201 Dowman Dr, Atlanta, GA 30322 USA
[5] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 07期
基金：
中国国家自然科学基金;
关键词：
C-H FUNCTIONALIZATION; TERMINAL ALKENES; RECENT PROGRESS; TRIFLUOROMETHYLATION; DIFLUOROACETYLATION; FLUOROALKYLATION; INHIBITORS; CHEMISTRY; ARYLATION; FLUORINE;
D O I：
10.1039/c7qo00119c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper-catalyzed gem-difluoromethylenation of the C(sp(2))-H bonds of alkenes with high functional group tolerance has been developed. This protocol is the first to efficiently achieve gem-difluoromethylenation of C(sp(2))-H bonds of unactivated aliphatic terminal olefins and can be applied in a reaction cascade to achieve gem-difluoromethylenation/cyclization of alkenes.
引用
收藏
页码：1239 / 1243
页数：5
相关论文
共 50 条
  • [1] Copper-catalyzed phosphorylation of sp2 C-H bonds
    Wang, Shan
    Guo, Rui
    Wang, Gao
    Chen, Shan-Yong
    Yu, Xiao-Qi
    CHEMICAL COMMUNICATIONS, 2014, 50 (84) : 12718 - 12721
  • [2] Copper-catalyzed direct acyloxylation of C(sp2)-H bonds with Benzoic acids
    Sheng Zhao
    Fa-Jie Chen
    Bin Liu
    Bing-Feng Shi
    Science China Chemistry, 2015, 58 : 1302 - 1309
  • [3] Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)-H Bonds of Benzamides
    Chabrier, Amelie
    Bruneau, Alexandre
    Benmahdjoub, Sara
    Benmerad, Belkacem
    Belaid, Sabrina
    Brion, Jean-Daniel
    Alami, Mouad
    Messaoudi, Samir
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (42) : 15006 - 15010
  • [4] Copper-catalyzed direct acyloxylation of C(sp2)-H bonds with Benzoic acids
    Zhao, Sheng
    Chen, Fa-Jie
    Liu, Bin
    Shi, Bing-Feng
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1302 - 1309
  • [5] Copper-Catalyzed Direct Acyloxylation of C(sp2)-H Bonds in Aromatic Amides
    Wang, Feifan
    Hu, Qiyan
    Shu, Chao
    Lin, Zhiyang
    Min, Dewen
    Shi, Tianchao
    Zhang, Wu
    ORGANIC LETTERS, 2017, 19 (13) : 3636 - 3639
  • [6] Copper-Catalyzed C(sp2)-C(sp2) Bond Formation via Single C(sp2)-H Activation
    Parmar, Himanshu V.
    Adodariya, Yash J.
    Patel, Unnati P.
    Shrivastav, Pranav S.
    Maru, Jayesh J.
    CHEMISTRYSELECT, 2024, 9 (02):
  • [7] Copper-Catalyzed Radical Allene C(sp2)-H Cyanation
    Wei, Youhao
    Wang, Zheng
    Wang, Kaifeng
    Qiu, Jiang-Kai
    Wang, Zhaoshan
    Li, Haotian
    Duan, Xiu
    Guo, Kai
    Bao, Xiaoguang
    Wu, Xinxin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (03)
  • [8] Copper-Catalyzed C(sp2)-H Amidation with Azides as Amino Sources
    Peng, Jiangling
    Xie, Zeqiang
    Chen, Ming
    Wang, Jian
    Zhu, Qiang
    ORGANIC LETTERS, 2014, 16 (18) : 4702 - 4705
  • [9] Copper-catalyzed arylation, vinylation and alkynylation of sp2 and sp3 C-H bonds with iodonium salts
    Liu, Chuan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [10] Rh-catalyzed intramolecular sp2 C-H bond difluoromethylenation
    Li, Yajun
    Zhu, Jiangtao
    Xie, Haibo
    Li, Shan
    Peng, Dongjie
    Li, Zhengke
    Wu, Yongming
    Gong, Yuefa
    CHEMICAL COMMUNICATIONS, 2012, 48 (25) : 3136 - 3138
12345