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

被引：50
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
来源：
CATALYSIS SCIENCE & TECHNOLOGY | 2019年 / 9卷 / 08期
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
相关论文
共 81 条
[51]   First-Row Transition-Metal Chloride Complexes of the Wide Bite-Angle Diphosphine iPrDPDBFphos and Reactivity Studies of Monovalent Nickel [J].
Marlier, Elodie E. ;
Tereniak, Stephen J. ;
Ding, Keying ;
Mulliken, Jenna E. ;
Lu, Connie C. .
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 [J].
Miyazaki, Satoshi ;
Koga, Yuji ;
Matsumoto, Taisuke ;
Matsubara, Kouki .
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 [J].
Nagao, Shinya ;
Matsumoto, Taisuke ;
Koga, Yuji ;
Matsubara, Kouki .
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 [J].
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. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) :2158-2167
[55]   Catalytic Reductive Vinylidene Transfer Reactions [J].
Pal, Sudipta ;
Zhou, You-Yun ;
Uyeda, Christopher .
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 [J].
Pappas, Iraklis ;
Treacy, Sean ;
Chirik, Paul 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 [J].
Phapale, Vilas B. ;
Guisan-Ceinos, Manuel ;
Bunuel, Elena ;
Cardenas, Diego J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) :12681-12688
[58]   Modulation of Nickel Pyridinedicarboxamidate Complexes to Explore the Properties of High-valent Oxidants [J].
Pirovano, Paolo ;
Twamley, Brendan ;
McDonald, Aidan R. .
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 [J].
Pirovano, Paolo ;
Berry, Abigail R. ;
Swart, Marcel ;
McDonald, Aidan R. .
DALTON TRANSACTIONS, 2018, 47 (01) :246-250
[60]   Tuning the Reactivity of Terminal Nickel(III)-Oxygen Adducts for C-H Bond Activation [J].
Pirovano, Paolo ;
Farquhar, Erik R. ;
Swart, Marcel ;
McDonald, Aidan R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (43) :14362-14370
123456789