Nickel-Catalyzed Multicomponent Carbodifluoroalkylation of Electron-Deficient Alkenes

被引:27
|
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
  • [1] Nickel-catalyzed organozinc-promoted carbocyclizations of electron-deficient alkenes with tethered unsaturation
    Montgomery, J
    Oblinger, E
    Savchenko, AV
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) : 4911 - 4920
  • [2] Nickel-Catalyzed Three-Component Reductive Alkylacylation of Electron-Deficient Activated Alkenes
    Wang, Lin
    Wang, Chuan
    ORGANIC LETTERS, 2020, 22 (22) : 8829 - 8835
  • [3] Enantioselective nickel-catalyzed anti-arylmetallative cyclizations onto acyclic electron-deficient alkenes
    Gillbard, Simone M.
    Green, Harley
    Argent, Stephen P.
    Lam, Hon Wai
    CHEMICAL COMMUNICATIONS, 2021, 57 (36) : 4436 - 4439
  • [4] Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes
    Li, Ze-Lin
    Wu, Peng-Yu
    Cai, Chun
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (08) : 3462 - 3468
  • [5] Overview on nickel-catalyzed electrochemical conjugate addition of organic halides on electron-deficient olefins
    Condon, S
    Nédélec, JY
    SYNTHESIS-STUTTGART, 2004, (18): : 3070 - 3078
  • [6] Coordination-Controlled Nickel-Catalyzed Benzylic Allylation of Unactivated Electron-Deficient Heterocycles
    Zhang, Pengpeng
    Wang, Jin
    Robertson, Zoe R.
    Newhouse, Timothy R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (22)
  • [7] NICKEL-CATALYZED REACTIONS INVOLVING STRAINED BONDS .12. NICKEL(0)-CATALYZED REACTION OF QUADRICYCLANE WITH ELECTRON-DEFICIENT OLEFINS
    NOYORI, R
    UMEDA, I
    KAWAUCHI, H
    TAKAYA, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) : 812 - 820
  • [8] Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes
    Wang, Hengbin
    Guptill, David M.
    Varela-Alvarez, Adrian
    Musaev, Djamaladdin G.
    Davies, Huw M. L.
    CHEMICAL SCIENCE, 2013, 4 (07) : 2844 - 2850
  • [9] Nickel-Catalyzed Dicarbofunctionalization of Alkenes
    Qi, Xiaoxu
    Diao, Tianning
    ACS CATALYSIS, 2020, 10 (15): : 8542 - 8556
  • [10] Mechanistic insights into aryl nickel-catalyzed benzylic dehydrogenation of electron-deficient heteroarenes by using DFT calculations
    Jia, Feiyun
    Zhang, Bo
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (37) : 17398 - 17406