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
[1]   Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactions [J].
Albisson, DA ;
Bedford, RB ;
Lawrence, SE ;
Scully, PN .
CHEMICAL COMMUNICATIONS, 1998, (19) :2095-2096
[2]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[3]   Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201
[4]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[5]  
Altenhoff G., 2003, ANGEW CHEM-GER EDIT, V115, P3818, DOI DOI 10.1002/ANGE.200351325
[6]  
[Anonymous], 2002, ANGEW CHE
[7]  
[Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22
[8]  
[Anonymous], 2002, J ORGANOMET CHEM
[9]   DIBENZO[A,E]CYCLOOCTATETRAENE IN A PROPOSED TEST FOR HETEROGENEITY IN CATALYSTS FORMED FROM SOLUBLE PLATINUM GROUP METAL-COMPLEXES [J].
ANTON, DR ;
CRABTREE, RH .
ORGANOMETALLICS, 1983, 2 (07) :855-859
[10]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534