Transition metal-catalyzed electrochemical processes for C-C bond formation

被引:13
|
作者
Torabi, Sara [1 ]
Jamshidi, Mahdi [2 ]
Amooshahi, Parvaneh [1 ]
Mehrdadian, Maryam [1 ]
Khazalpour, Sadegh [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Hamadan, Iran
[2] Hamadan Univ Med Sci, Sch Pharm, Dept Toxicol & Pharmacol, Hamadan, Hamadan, Iran
关键词
H FUNCTIONALIZATION; ARYL HALIDES; ELECTROREDUCTIVE CYCLIZATION; REFORMATSKY REACTION; CARBONYL-COMPOUNDS; ORGANIC HALIDES; NICKEL; ALLYLATION; ALKYL; ELECTROSYNTHESIS;
D O I
10.1039/d0nj03450a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this review article, thein situformation of various organometallic reagents by electrochemical methods for addition (carbon-carbon bond) reactions is discussed. In this study, the organometallic complexes are formed by the insertion of a metal in an alkyl or allyl halide structure. Furthermore, the catalytic cycles of the studied metals on the surface of electrodes and in solutions may consist of oxidative addition, the reductive elimination of ligands, metal transformation, the production of metal ions, or cyclization processes. Different types of C-C bond formation, such as Csp(2)-Csp(2), Csp(2)-Csp(3), and Csp(3)-Csp(3), using transition metal-catalyzed and electrochemical approaches (organometallic electrochemistry) are discussed. Moreover, variety of metals, such as Zn, Ni, Sm, In, Mn, Ru, Pd, Fe, and Cr, are investigated as catalysts in the formation of C-C bonds between two organic compounds. High atom economy; excellent isolated yields; sustainability; scalability; one-pot, simple, and mild reaction conditions; and the non-toxicity of reagents are known as some unique features of the electrochemical protocols for the synthesis of organic compounds. In recent years, organometallic electrochemical reactions have aided the formation of one of the most important bonds in the synthesis of new molecules. Some of the most famous of these protocols are the metal-catalyzed or metal-mediated electrochemical Barbier, Nozaki-Hiyama-Kishi, Reformatsky, and Barbier-Grignard-type reactions. This review offers an overview of the application of strategies and methodologies based on electrochemical methods and metal catalysts for the allylation and alkylation of chemical compounds.
引用
收藏
页码:15321 / 15336
页数:16
相关论文
共 50 条
  • [41] Transition Metal-Catalyzed Regio-selective Aromatic C-H Bond Oxidation for C-O Bond Formation
    Yang, Fanzhi
    Zhang, Han
    Liu, Xuri
    Wang, Bo
    Lutz, Ackermann
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (01) : 59 - 73
  • [42] Heterocycle Construction via Transition Metal-Catalyzed C-H Functionalization and C-Heteroatom Bond Formation
    Liu, Yajun
    Kim, Jihye
    Chae, Junghyun
    CURRENT ORGANIC CHEMISTRY, 2014, 18 (16) : 2049 - 2071
  • [43] Metal-catalyzed C-C bond forming reactions involving boron-stabilized organometallic nucleophiles
    Meek, Simon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [44] Recent Advances in Transition-metal-catalyzed C-C Bond Formation via C(sp2)-F Bond Cleavage
    Fu, Liyan
    Chen, Qiang
    Nishihara, Yasushi
    CHEMICAL RECORD, 2021, 21 (12): : 3394 - 3410
  • [45] Progress of the C-C Bond Cleavage in Acetonitrile Catalyzed by Transition-Metal Complexes
    Chen Hui-Qing
    Zhang Kun
    Xu Feng
    Huang Wei
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2013, 29 (11) : 2265 - 2275
  • [46] Transition metal-catalyzed C-H/C-C activation and coupling with 1,3-diyne
    Pati, Bedadyuti Vedvyas
    Puthalath, Nitha Nahan
    Banjare, Shyam Kumar
    Nanda, Tanmayee
    Ravikumar, Ponneri C. C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (14) : 2842 - 2869
  • [47] Chiral metal nanoparticle-catalyzed asymmetric C-C bond formation reactions
    Yasukawa, Tomohiro
    Miyamura, Hiroyuki
    Kobayashi, Shu
    CHEMICAL SOCIETY REVIEWS, 2014, 43 (05) : 1450 - 1461
  • [48] NEW TRANSITION METAL-CATALYZED C-C COUPLING REACTIONS INITIATED BY C-X BOND-CLEAVAGE AND TERMINATED BY H-TRANSFER
    CATELLANI, M
    CHIUSOLI, GP
    GIROLDINI, W
    SALERNO, G
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 199 (01) : C21 - C23
  • [49] Forging Amides Through Metal-Catalyzed C-C Coupling with Isocyanates
    Serrano, Eloisa
    Martin, Ruben
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (24) : 3051 - 3064
  • [50] Transition-Metal-Catalyzed C-C Bond Macrocyclization via Intramolecular C-H Bond Activation
    Wang, Xiao
    Lu, Ming-Zhu
    Loh, Teck-Peng
    CATALYSTS, 2023, 13 (02)