Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation

被引:54
作者
Nett, Alex J. [1 ]
Canellas, Santiago [1 ,2 ]
Higuchi, Yuki [1 ]
Robo, Michael T. [1 ]
Kochkodan, Jeanne M. [1 ]
Haynes, M. Taylor, II [1 ,3 ]
Kampf, Jeff W. [1 ]
Montgomery, John [1 ]
机构
[1] Univ Michigan, Dept Chem, 930 North Univ Ave, Ann Arbor, MI 48019 USA
[2] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Avda Paisos Catalans 16, E-43007 Tarragona, Spain
[3] Dept Chem & Biochem, 1 Grand Ave, San Luis Obispo, CA 93405 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
precatalyst; amination; reductive coupling; N-heterocyclic carbenes; catalysis; CROSS-COUPLING REACTIONS; HETEROCYCLIC CARBENE; H FUNCTIONALIZATION; COMPLEXES; PRECATALYST; LIGAND; ARYL; AMINATION; CHLORIDES; PALLADIUM;
D O I
10.1021/acscatal.8b02187
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 synthesis and catalytic activity of several classes of NHC-Ni(0) precatalysts stabilized by electron withdrawing alkenes are described. Variations in the structure of fumarate and acrylate ligands modulate the reactivity and stability of the NHC-Ni(0) precatalysts and lead to practical and versatile catalysts for a variety of transformations. The catalytic activity and efficiency of representative members of this class of catalysts have been evaluated in reductive couplings of aldehydes and alkynes and in N-arylations of amines.
引用
收藏
页码:6606 / 6611
页数:11
相关论文
共 46 条
[21]   A Two-Coordinate Nickel Imido Complex That Effects C-H Amination [J].
Laskowski, Carl A. ;
Miller, Alexander J. M. ;
Hillhouse, Gregory L. ;
Cundari, Thomas R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (04) :771-773
[22]   Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design [J].
Lavoie, Christopher M. ;
MacQueen, Preston M. ;
Rotta-Loria, Nicolas L. ;
Sawatzky, Ryan S. ;
Borzenko, Andrey ;
Chisholm, Alicia J. ;
Hargreaves, Breanna K. V. ;
McDonald, Robert ;
Ferguson, Michael J. ;
Stradiotto, Mark .
NATURE COMMUNICATIONS, 2016, 7
[23]   Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols [J].
MacQueen, Preston M. ;
Tassone, Joseph P. ;
Diaz, Carlos ;
Stradiotto, Mark .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (15) :5023-5027
[24]   Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-Coupling [J].
Magano, Javier ;
Monfette, Sebastien .
ACS CATALYSIS, 2015, 5 (05) :3120-3123
[25]   An efficient silane-promoted nickel-catalyzed amination of aryl and heteroaryl chlorides [J].
Manolikakes, Georg ;
Gavryushin, Andrei ;
Knochel, Paul .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) :1429-1434
[26]   Efficient C-N and C-S Bond Formation Using the Highly Active [Ni(allyl)Cl(IPr*OMe)] Precatalyst [J].
Martin, Anthony R. ;
Nelson, David J. ;
Meiries, Sebastien ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (15) :3127-3131
[27]   Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis [J].
Martin, Anthony R. ;
Makida, Yusuke ;
Meiries, Sebastien ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
ORGANOMETALLICS, 2013, 32 (21) :6265-6270
[28]   Synthesis and structures of nickel halide complexes bearing mono- and bis-coordinated N-heterocyclic carbene ligands, catalyzing Grignard cross-coupling reactions [J].
Matsubara, Kouki ;
Ueno, Keita ;
Shibata, Youhei .
ORGANOMETALLICS, 2006, 25 (14) :3422-3427
[29]   Zerovalent palladium and nickel complexes of heterocyclic carbenes: Oxidative addition of organic halides, carbon-carbon coupling processes, and the Heck reaction [J].
McGuinness, DS ;
Cavell, KJ ;
Skelton, BW ;
White, AH .
ORGANOMETALLICS, 1999, 18 (09) :1596-1605
[30]   [Pd(IPr*OMe)(acac)Cl]: Tuning the N-Heterocyclic Carbene in Catalytic C-N Bond Formation [J].
Meiries, Sebastien ;
Speck, Klaus ;
Cordes, David B. ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
ORGANOMETALLICS, 2013, 32 (01) :330-339