Development of Preformed Pd Catalysts for Cross-Coupling Reactions, Beyond the 2010 Nobel Prize

被引:388
作者
Li, Hongbo [1 ]
Seechurn, Carin C. C. Johansson [2 ]
Colacot, Thomas J. [1 ]
机构
[1] Johnson Matthey Catalysis & Chiral Technol, W Deptford, NJ 08066 USA
[2] Johnson Matthey Catalysis & Chiral Technol, Royston SG8 5HE, Herts, England
关键词
cross-coupling; palladium; precatalysts; N-HETEROCYCLIC-CARBENE; C-O BOND; ACTIVE PALLADIUM CATALYSTS; AIR-STABLE CATALYSTS; ARYL CHLORIDES; ROOM-TEMPERATURE; DIRECT ARYLATION; ALPHA-ARYLATION; GENERAL-METHOD; HECK REACTIONS;
D O I
10.1021/cs300082f
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
Strategies for the development of Pd catalysts based on utilization of L2Pd and LPd species, beyond the contributions of the 2010 Nobel Laureates Richard Heck, Ei-ichi Negishi, and Akira Suzuki, along with their contemporaries, are reviewed. These well-defined, preformed Pd catalysts improve the selectivity and activity of selected cross-coupling reactions by reducing the metal loading and the ligand-to-metal ratios. This review describes predominantly the development of Pd precatalysts over the last 10 years and highlights the benefits often observed when using well-defined preformed catalysts relative to those generated in situ.
引用
收藏
页码:1147 / 1164
页数:18
相关论文
共 153 条
[1]   Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].
Ackermann, Lutz .
SYNLETT, 2007, (04) :507-526
[2]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]  
Amatore C., 1997, J AM CHEM SOC, V119, P5176
[5]   Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols [J].
Arentsen, K ;
Caddick, S ;
Geoffrey, F ;
Cloke, N ;
Herring, AP ;
Hitchcock, PB .
TETRAHEDRON LETTERS, 2004, 45 (17) :3511-3515
[6]   Carbonylation of aryl halides: Extending the scope of the reaction [J].
Barnard, Christopher F. J. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (04) :566-574
[7]   High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source [J].
Bedford, RB ;
Cazin, CSJ ;
Coles, SJ ;
Gelbrich, T ;
Horton, PN ;
Hursthouse, MB ;
Light, ME .
ORGANOMETALLICS, 2003, 22 (05) :987-999
[8]   First palladium-catalyzed aminations of aryl chlorides [J].
Beller, M ;
Riermeier, TH ;
Reisinger, CP ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1997, 38 (12) :2073-2074
[9]  
Beller M., 1995, ANGEW CHEM INT EDIT, V107, P1992
[10]   Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2009, 65 (50) :10269-10310