Short, facile, and high-yielding synthesis of extremely efficient pincer-type suzuki catalysts bearing aminoiphosphine substituents

被引:90
作者
Bolliger, Jeanne L. [1 ]
Blacque, Olivier [1 ]
Frech, Christian M. [1 ]
机构
[1] Univ Zurich, Dept Anrogan Chem, CH-8057 Zurich, Switzerland
关键词
C-C coupling; P ligands; palladium; phosphanes Suzuki; reaction;
D O I
10.1002/anie.200701804
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Feeling the pinch: Aryl bromides can be coupled with phenylboronic acid quantitatively within a few minutes by using pincer-type catalysts bearing aminophosphine substituents. [Pd(Cl) 2P(NR2)3] has been used as a template for the pincer core directly on the metal center (see scheme, NR2 = piperidinyl, X = NH or O), which makes the independent synthesis and purification of the air- and moisture-sensitive ligand systems unnecessary. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6514 / 6517
页数:4
相关论文
共 71 条
[21]   Synthesis of chiral binaphthalenes using the asymmetric Suzuki reaction [J].
Cammidge, AN ;
Crépy, KVL .
TETRAHEDRON, 2004, 60 (20) :4377-4386
[22]   The first asymmetric Suzuki cross-coupling reaction [J].
Cammidge, AN ;
Crépy, KVL .
CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724
[23]   Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium-chiral phosphine ratio [J].
Castanet, AS ;
Colobert, F ;
Broutin, PE ;
Obringer, M .
TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :659-665
[24]   The asymmetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds [J].
Cho, SY ;
Shibasaki, M .
TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3751-3754
[25]  
CLARK ML, 2002, CHEM COMMUN, P2065
[26]   High-throughput screening studies of fiber-supported catalysts leading to room-temperature Suzuki coupling [J].
Colacot, TJ ;
Gore, ES ;
Kuber, A .
ORGANOMETALLICS, 2002, 21 (16) :3301-3304
[27]   Insights into the Heck reaction with PCP pincer palladium(II) complexes [J].
Eberhard, MR .
ORGANIC LETTERS, 2004, 6 (13) :2125-2128
[28]   MECHANISM OF THERMAL-DECOMPOSITION OF DINEOPENTYLBIS(TRIETHYLPHOSPHINE)PLATINUM(II) - FORMATION OF BIS(TRIETHYLPHOSPHINE)-3,3-DIMETHYLPLATINACYCLOBUTANE [J].
FOLEY, P ;
DICOSIMO, R ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) :6713-6725
[29]   Redox-induced collapse and regeneration of a pincer-type complex framework: A nonplanar coordination mode of palladium(II) [J].
Frech, CM ;
Shimon, LJW ;
Milstein, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1709-1711
[30]  
FRECH CM, 2005, ANGEW CHEM, V117, P1737