Ni(I)-Ni(III) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(I) complexes

被引:48
作者
Inatomi, Takahiro [1 ]
Fukahori, Yukino [1 ]
Yamada, Yuji [1 ]
Ishikawa, Ryuta [1 ]
Kanegawa, Shinji [2 ]
Koga, Yuji [1 ]
Matsubara, Kouki [1 ]
机构
[1] Fukuoka Univ, Dept Chem, 8-19-1 Nanakuma, Fukuoka, Fukuoka 8140180, Japan
[2] Kyushu Univ, Inst Adv Mat Chem & Engn, 744 Motooka, Fukuoka, Fukuoka 8190395, Japan
基金
日本学术振兴会;
关键词
HETEROATOM BOND FORMATION; NICKEL(I) COMPLEXES; CATALYZED TRIFLUOROMETHYLTHIOLATION; OXIDATION-STATE; 3-COORDINATE; HALIDES; ACTIVATION; REACTIVITY; ELECTROPHILES; RELEVANT;
D O I
10.1039/c8cy02427h
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
Intermediate amide complexes of NHC-ligated monovalent nickel in Buchwald-Hartwig amination of aryl halides were isolated and structurally characterized. The amide complexes reacted with aryl bromide to form a cross-coupling product. Low-temperature observation of the oxidative addition product of the Ni(I) amide complex with aryl bromide indicated the presence of a Ni(III) intermediate. The results showed that a well-defined mononuclear NHC-Ni(I) complex can act as a key intermediate in homogeneous catalysis.
引用
收藏
页码:1784 / 1793
页数:10
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共 81 条
  • [51] First-Row Transition-Metal Chloride Complexes of the Wide Bite-Angle Diphosphine iPrDPDBFphos and Reactivity Studies of Monovalent Nickel
    Marlier, Elodie E.
    Tereniak, Stephen J.
    Ding, Keying
    Mulliken, Jenna E.
    Lu, Connie C.
    [J]. INORGANIC CHEMISTRY, 2011, 50 (19) : 9290 - 9299
  • [52] A new aspect of nickel-catalyzed Grignard cross-coupling reactions: selective synthesis, structure, and catalytic behavior of a T-shape three-coordinate nickel(I) chloride bearing a bulky NHC ligand
    Miyazaki, Satoshi
    Koga, Yuji
    Matsumoto, Taisuke
    Matsubara, Kouki
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (11) : 1932 - 1934
  • [53] Monovalent Nickel Complex Bearing a Bulky N-Heterocyclic Carbene Catalyzes Buchwald-Hartwig Amination of Aryl Halides under Mild Conditions
    Nagao, Shinya
    Matsumoto, Taisuke
    Koga, Yuji
    Matsubara, Kouki
    [J]. CHEMISTRY LETTERS, 2011, 40 (09) : 1036 - 1038
  • [54] Three-Coordinate Nickel(I) Complexes Stabilised by Six-, Seven- and Eight-Membered Ring N-Heterocyclic Carbenes: Synthesis, EPR/DFT Studies and Catalytic Activity
    Page, Michael J.
    Lu, Wei Y.
    Poulten, Rebecca C.
    Carter, Emma
    Algarra, Andres G.
    Kariuki, Benson M.
    Macgregor, Stuart A.
    Mahon, Mary F.
    Cavell, Kingsley J.
    Murphy, Damien M.
    Whittlesey, Michael K.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) : 2158 - 2167
  • [55] Catalytic Reductive Vinylidene Transfer Reactions
    Pal, Sudipta
    Zhou, You-Yun
    Uyeda, Christopher
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (34) : 11686 - 11689
  • [56] Alkene Hydrosilylation Using Tertiary Silanes with α-Diimine Nickel Catalysts. Redox-Active Ligands Promote a Distinct Mechanistic Pathway from Platinum Catalysts
    Pappas, Iraklis
    Treacy, Sean
    Chirik, Paul J.
    [J]. ACS CATALYSIS, 2016, 6 (07): : 4105 - 4109
  • [57] Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp2)-C(sp3) Bonds: Scope and Mechanism
    Phapale, Vilas B.
    Guisan-Ceinos, Manuel
    Bunuel, Elena
    Cardenas, Diego J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) : 12681 - 12688
  • [58] Modulation of Nickel Pyridinedicarboxamidate Complexes to Explore the Properties of High-valent Oxidants
    Pirovano, Paolo
    Twamley, Brendan
    McDonald, Aidan R.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (20) : 5238 - 5245
  • [59] Indirect evidence for a NiIII-oxyl oxidant in the reaction of a NiII complex with peracid
    Pirovano, Paolo
    Berry, Abigail R.
    Swart, Marcel
    McDonald, Aidan R.
    [J]. DALTON TRANSACTIONS, 2018, 47 (01) : 246 - 250
  • [60] Tuning the Reactivity of Terminal Nickel(III)-Oxygen Adducts for C-H Bond Activation
    Pirovano, Paolo
    Farquhar, Erik R.
    Swart, Marcel
    McDonald, Aidan R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (43) : 14362 - 14370