Synthesis of Fluorinated Compounds by Nickel-Catalyzed Defluorinative Cross-Coupling Reactions

被引:33
|
作者
Wang, Kuai [1 ]
Kong, Wangqing [2 ]
机构
[1] Huaibei Normal Univ, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ, Huaibei 235000, Anhui, Peoples R China
[2] Wuhan Univ, Inst Adv Studies IAS, Wuhan 430072, Hubei, Peoples R China
基金
中国博士后科学基金;
关键词
nickel catalysis; organofluorine compounds; C-F bond activation; defluorinative cross-coupling; aryl fluorides; gem-difluoroalkenes; trifluoromethyl compounds; C-F BOND; GEM-DIFLUOROALKENES; GRIGNARD-REAGENTS; ARYL FLUORIDES; ASYMMETRIC FLUORINATION; TRIFLUOROMETHYL ALKENES; ACTIVATION REACTIONS; ORGANOZINC REAGENTS; OXIDATIVE ADDITION; 3+2 CYCLOADDITION;
D O I
10.1021/acscatal.3c02993
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
Organofluorine compounds have attracted extensive attention in various industrial fields due to their unique chemical and physical properties. Despite increasing demand in a wide range of scientific fields, the synthesis of organofluorine compounds still faces several problems, such as difficulties in the handling of fluorinating reagents and the control of chemoselectivity. Compared with the formation of C-F bonds, the activation and functionalization of carbon-fluorine bonds is a very important but challenging topic in synthetic chemistry. Due to the unique properties of nickel, Ni-catalyzed defluorinative cross-couplings have been greatly developed in the past few decades as powerful strategies for the construction of fluorinated organic compounds. This Review summarizes important advances in the Ni-catalyzed defluorinative cross-coupling of aryl fluorides, gem-difluorovinyl and trifluoromethyl compounds.
引用
收藏
页码:12238 / 12268
页数:31
相关论文
共 50 条
  • [1] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling
    Lan, Yun
    Yang, Feiyan
    Wang, Chuan
    ACS CATALYSIS, 2018, 8 (10): : 9245 - 9251
  • [2] π-Complexation in Nickel-Catalyzed Cross-Coupling Reactions
    Sontag, S. Kyle
    Bilbrey, Jenna A.
    Huddleston, N. Eric
    Sheppard, Gareth R.
    Allen, Wesley D.
    Locklin, Jason
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (04) : 1836 - 1841
  • [3] Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions
    Diccianni, Justin B.
    Diao, Tianning
    TRENDS IN CHEMISTRY, 2019, 1 (09): : 830 - 844
  • [4] Synthetic Applications of Nickel-Catalyzed Cross-Coupling and Cyclisation Reactions
    Durandetti, Muriel
    CHEMICAL RECORD, 2021, 21 (12) : 3746 - 3757
  • [5] Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions
    Poremba, Kelsey E.
    Dibrell, Sara E.
    Reisman, Sarah E.
    ACS CATALYSIS, 2020, 10 (15): : 8237 - 8246
  • [6] Nickel-catalyzed carbonylative Negishi cross-coupling reactions
    Wang, Qiaoling
    Chen, Chuo
    TETRAHEDRON LETTERS, 2008, 49 (18) : 2916 - 2921
  • [7] Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers and Esters
    Tollefson, Emily J.
    Hanna, Luke E.
    Jarvo, Elizabeth R.
    ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (08) : 2344 - 2353
  • [8] Nickel-catalyzed defluorinative alkylation of C(sp2)-F bonds
    Tong, Xue
    Luo, Si-Si
    Shen, Hua
    Zhang, Shu
    Cao, Tian
    Luo, Yi-Peng
    Huang, Long-Ling
    Ma, Xi-Tao
    Liu, Xiang-Wei
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (16) : 4533 - 4542
  • [9] Nickel-catalyzed Suzuki-Miyaura type cross-coupling reactions of (2,2-difluorovinyl)benzene derivatives with arylboronic acids
    Xiong, Yang
    Huang, Tao
    Ji, Xinfei
    Wu, Jingjing
    Cao, Song
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (27) : 7389 - 7392
  • [10] Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
    Heijnen, Dorus
    Gualtierotti, Jean-Baptiste
    Hornillos, Valentin
    Feringa, Ben L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (12) : 3991 - 3995