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
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
  • [1] [Anonymous], 2015, CRYSTALSTRUCTURE VER
  • [2] [Anonymous], J AM CHEM SOC
  • [3] [Anonymous], TETRAHEDRON
  • [4] [Anonymous], CHEM COMMUN
  • [5] [Anonymous], ORGANOMETALLICS
  • [6] [Anonymous], 2017, Angew. Chem., DOI DOI 10.1002/ANGE.201706423
  • [7] 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
  • [8] Photoinduced energy-transfer dynamics in multichromophoric arrays containing transition metal complexes and organic modules
    Barbieri, Andrea
    Ventura, Barbara
    Ziessel, Raymond
    [J]. COORDINATION CHEMISTRY REVIEWS, 2012, 256 (15-16) : 1732 - 1741
  • [9] Disproportionation Reactions of an Organometallic Ni(I) Amidate Complex: Scope and Mechanistic Investigations
    Beattie, D. Dawson
    Lascoumettes, Gautier
    Kennepohl, Pierre
    Love, Jennifer A.
    Schafer, Laurel L.
    [J]. ORGANOMETALLICS, 2018, 37 (09) : 1392 - 1399
  • [10] Oxidation State Dependent Coordination Modes: Accessing an Amidate-Supported Nickel( I) δ-bis(C-H) Agostic Complex
    Beattie, D. Dawson
    Bowes, Eric G.
    Drover, Marcus W.
    Love, Jennifer A.
    Schafer, Laurel L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (42) : 13290 - 13295
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