Reactions of nickel(0) with organochlorides, organobromides, and organoiodides: mechanisms and structure/reactivity relationships

被引:44
作者
Greaves, Megan E. [1 ,2 ]
Johnson Humphrey, Elliot L. B. [1 ]
Nelson, David J. [1 ]
机构
[1] Univ Strathclyde, WestCHEM Dept Pure & Appl Chem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland
[2] AstraZeneca, Chem Dev Pharmaceut Technol & Dev, Operat, Macclesfield SK10 2NA, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
Substrates - Catalysis - Organic compounds - Phosphorus compounds - Nickel compounds;
D O I
10.1039/d1cy00374g
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 reactions of nickel(0) complexes with organohalides have been reviewed. The review is divided according to the class of ligand that is present on nickel: phosphine, N-heterocyclic carbene, or bidentate nitrogen ligand. The preferred mechanism of reaction is often determined by a delicate balance of ligand and substrate structure, and relatively small changes can lead to large differences in behaviour. This will have an impact on the progress of catalytic reactions that use organohalide substrates, and may influence ligand selection and/or the scope and limitations of the reaction.
引用
收藏
页码:2980 / 2996
页数:17
相关论文
共 92 条
  • [1] MECHANISM OF OXIDATIVE ADDITION OF PALLADIUM(0) WITH AROMATIC IODIDES IN TOLUENE, MONITORED AT ULTRAMICROELECTRODES
    AMATORE, C
    PFLUGER, F
    [J]. ORGANOMETALLICS, 1990, 9 (08) : 2276 - 2282
  • [2] RATES AND MECHANISM OF BIPHENYL SYNTHESIS CATALYZED BY ELECTROGENERATED COORDINATIVELY UNSATURATED NICKEL-COMPLEXES
    AMATORE, C
    JUTAND, A
    [J]. ORGANOMETALLICS, 1988, 7 (10) : 2203 - 2214
  • [3] Nickel: The "Spirited Horse" of Transition Metal Catalysis
    Ananikov, Valentine P.
    [J]. ACS CATALYSIS, 2015, 5 (03): : 1964 - 1971
  • [4] [Anonymous], 1972, J CRYST MOL STRUCT
  • [5] Bond Activation with Low-Valent Nickel in Homogeneous Systems
    Arevalo, Alma
    Garcia, Juventino J.
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (26) : 4063 - 4074
  • [6] Oxidative Addition of Aryl Electrophiles to a Prototypical Nickel(0) Complex: Mechanism and Structure/Reactivity Relationships
    Bajo, Sonia
    Laidlaw, Gillian
    Kennedy, Alan R.
    Sproules, Stephen
    Nelson, David J.
    [J]. ORGANOMETALLICS, 2017, 36 (08) : 1662 - 1672
  • [7] Bis(dialkylphosphino)ferrocene-Ligated Nickel(II) Precatalysts for Suzuki-Miyaura Reactions of Aryl Carbonates
    Barth, Emily L.
    Davis, Ryan M.
    Beromi, Mepn Mohadjer
    Walden, Andrew G.
    Balcells, David
    Brudvig, Gary W.
    Dardir, Amira H.
    Hazari, Nilay
    Lant, Hannah M. C.
    Mercado, Brandon Q.
    Peczak, Ian L.
    [J]. ORGANOMETALLICS, 2019, 38 (17) : 3377 - 3387
  • [8] Synthesis and Reactivity of Paramagnetic Nickel Polypyridyl Complexes Relevant to C(sp2)-C(sp3)Coupling Reactions
    Beromi, Megan Mohadjer
    Brudvig, Gary W.
    Hazari, Nilay
    Lant, Hannah M. C.
    Mercado, Brandon Q.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (18) : 6094 - 6098
  • [9] Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species
    Beromi, Megan Mohadjer
    Nova, Ainara
    Balcells, David
    Brasacchio, Ann M.
    Brudvig, Gary W.
    Guard, Louise M.
    Hazari, Nilay
    Vinyard, David J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (02) : 922 - 936
  • [10] Ring-Walking of Zerovalent Nickel on Aryl Halides
    Bilbrey, Jenna A.
    Bootsma, Andrea N.
    Bartlett, Marcus A.
    Locklin, Jason
    Wheeler, Steven E.
    Allen, Wesley D.
    [J]. JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2017, 13 (04) : 1706 - 1711