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
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 [J].
Bajo, Sonia ;
Laidlaw, Gillian ;
Kennedy, Alan R. ;
Sproules, Stephen ;
Nelson, David J. .
ORGANOMETALLICS, 2017, 36 (08) :1662-1672
[8]   Photoinduced energy-transfer dynamics in multichromophoric arrays containing transition metal complexes and organic modules [J].
Barbieri, Andrea ;
Ventura, Barbara ;
Ziessel, Raymond .
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (15-16) :1732-1741
[9]   Disproportionation Reactions of an Organometallic Ni(I) Amidate Complex: Scope and Mechanistic Investigations [J].
Beattie, D. Dawson ;
Lascoumettes, Gautier ;
Kennepohl, Pierre ;
Love, Jennifer A. ;
Schafer, Laurel L. .
ORGANOMETALLICS, 2018, 37 (09) :1392-1399
[10]   Oxidation State Dependent Coordination Modes: Accessing an Amidate-Supported Nickel( I) δ-bis(C-H) Agostic Complex [J].
Beattie, D. Dawson ;
Bowes, Eric G. ;
Drover, Marcus W. ;
Love, Jennifer A. ;
Schafer, Laurel L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (42) :13290-13295