Nickel-Catalyzed Multicomponent Carbodifluoroalkylation of Electron-Deficient Alkenes

被引:28
作者
Rao, Na [1 ]
Li, Yun-Ze [1 ]
Luo, Yun-Cheng [1 ]
Zhang, Yanxia [1 ]
Zhang, Xingang [1 ,2 ]
机构
[1] Univ Chinese Academy Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Univ Chinese Acad Sci, Hangzhou Inst Advanced Study, Sch Chem & Mat Sci, Hangzhou 310024, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
carbonylation; dicarbofunctionalization; difluoroalkylation; electron-deficient alkenes; nickel catalysis; ETHYL BROMODIFLUOROACETATE; COUPLING SYNTHESIS; CARBONYLATION; ALKYL; TRIFLUOROMETHYLATION; FLUORINATION; KETONES;
D O I
10.1021/acscatal.2c06149
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The nickel-catalyzed multicomponent dicarbofunc-tionalization of alkenes represents one of the most straightforward approaches to complex organofluorine compounds. However, the catalytic carbofluoroalkylation of electron-deficient alkenes remains underdeveloped. Here, we report a nickel-catalyzed three -component aryldifluoroalkylation of industry-relevant acrylonitrile and acrylate with arylboronic acids and difluoroalkyl halides. The reaction can extend to a four-component nickel-catalyzed carbonylation reaction under 1 atm CO gas. This modular catalytic synthesis features synthetic convenience, high functional group tolerance, and simple components to construct complex difluoroalkylated compounds expediently. The synthetic utility has also been demonstrated by the diversified transformations of the resulting products into medicinal interest fluorinated compounds.
引用
收藏
页码:4111 / 4119
页数:9
相关论文
共 50 条
  • [31] Visible-light photoredox catalyzed hydroacylation of electron-deficient alkenes: carboxylic anhydride as an acyl radical source
    Dong, Shupeng
    Wu, Guibing
    Yuan, Xiaoqian
    Zou, Chuncheng
    Ye, Jinxing
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2230 - 2234
  • [32] Salt-Stabilized Silylzinc Pivalates for Nickel-Catalyzed Carbosilylation of Alkenes
    Wang, Jixin
    Duan, Zhili
    Liu, Xingchen
    Dong, Shoucheng
    Chen, Kaixin
    Li, Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (17)
  • [33] Dual Photoredox/Nickel-Catalyzed Three-Component Carbofunctionalization of Alkenes
    Garcia-Dominguez, Andres
    Mondal, Rahul
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) : 12286 - 12290
  • [34] Stereoselective Synthesis of Trisubstituted Alkenes by Nickel-Catalyzed Benzylation and Alkene Isomerization
    Zhao, Yunlong
    Liu, Chen-Fei
    Lin, Leroy Qi Hao
    Chan, Albert S. C.
    Koh, Ming Joo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (26)
  • [35] Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes
    Wu, Xianqing
    Turlik, Aneta
    Luan, Baixue
    He, Feng
    Qu, Jingping
    Houk, K. N.
    Chen, Yifeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (36)
  • [36] Visible-Light Mediated Nickel-Catalyzed Asymmetric Difunctionalizations of Alkenes
    Zhao, Han-Tong
    Lin, Jia-Ni
    Shu, Wei
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (67)
  • [37] Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes
    Xie, Leipeng
    Wang, Shenghao
    Zhang, Lanlan
    Zhao, Lei
    Luo, Chun
    Mu, Linping
    Wang, Xiuguang
    Wang, Chao
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [38] Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
    Larionova, Natalia A.
    Ondozabal, Jun Miyatake
    Cambeiro, Xacobe C.
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 558 - 564
  • [39] Halogenation of Electron-Deficient Vicinal Substituted Alkenes: Regio- and Stereoselectivity
    Zubkov, Ilya N.
    Ushakov, Igor A.
    Chipanina, Nina N.
    Rulev, Alexander Yu.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4130 - 4133
  • [40] Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes
    Talavera, Laura
    Freund, Robert R. A.
    Zhang, Huihui
    Wakeling, Matthew
    Jensen, Mara
    Martin, Ruben
    ACS CATALYSIS, 2023, 13 (08) : 5538 - 5543