Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki-Miyaura coupling catalysts

被引:49
作者
Mahamo, Tebello [1 ,3 ]
Mogorosi, Mokgolela M. [1 ]
Moss, John R. [1 ]
Mapolie, Selwyn F. [2 ]
Slootweg, J. Chris [3 ]
Lammertsma, Koop [3 ]
Smith, Gregory S. [1 ]
机构
[1] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa
[2] Univ Stellenbosch, Dept Chem & Polymer Sci, Matieland, South Africa
[3] Vrije Univ Amsterdam, Fac Sci, Dept Chem & Pharmaceut Sci, NL-1081 HV Amsterdam, Netherlands
基金
新加坡国家研究基金会;
关键词
Arylboronic acids; Aryl halides; Suzuki-Miyaura coupling; Iminophosphines; Palladium(II) complexes; METAL-COMPLEXES; HECK REACTION; IMINOPHOSPHINE LIGANDS; PLATINUM(II) COMPLEXES; DONOR SETS; PHOSPHINE; REACTIVITY; TRANSMETALATION; OLIGOMERIZATION; HYDROGENATION;
D O I
10.1016/j.jorganchem.2011.12.021
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Palladium(II) complexes of the general formulae [PdCl2((PN)-N-boolean AND)] and [Pd(Me)Cl((PN)-N-boolean AND)] were obtained from bidentate ligands bearing phosphine and imine donor groups. The complexes were shown to be highly active catalysts for the Suzuki-Miyaura cross-coupling reaction. The complexes are tolerant of a wide variety of reaction conditions such as solvent, choice of base as well as substituents on both arylboronic acids and aryl halides. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:34 / 42
页数:9
相关论文
共 77 条
[1]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[2]   Methyl-, acetyl- and allyl-palladium and -platinum complexes containing the novel chiral phosphorus-imine 2-(diphenylphosphino)benzylidene-S(-)-alpha-methyl-benzylamine ligand [J].
Ankersmit, HA ;
Loken, BH ;
Kooijman, H ;
Spek, AL ;
Vrieze, K ;
vanKoten, G .
INORGANICA CHIMICA ACTA, 1996, 252 (1-2) :141-155
[3]  
[Anonymous], 2006, SAINT VERS 7 60A
[4]   Effect of the leaving ligand X on transmetalation of organostannanes (vinylSnR3) with LnPd(Ar)(X) in Stille cross-coupling reactions.: A density functional theory study [J].
Ariafard, Alireza ;
Lin, Zhenyang ;
Fairlamb, Ian J. S. .
ORGANOMETALLICS, 2006, 25 (24) :5788-5794
[5]   Molecular graphics: From science to art [J].
Atwood, JL ;
Barbour, LJ .
CRYSTAL GROWTH & DESIGN, 2003, 3 (01) :3-8
[6]   SYNTHESIS OF ORGANOMETALLIC PALLADIUM COMPLEXES - AN UNDERGRADUATE EXPERIMENT [J].
BAILEY, CT ;
LISENSKY, GC .
JOURNAL OF CHEMICAL EDUCATION, 1985, 62 (10) :896-897
[7]  
Barbour L.J., 2001, J SUPRAMOL CHEM, V1, P189, DOI [DOI 10.1016/S1472-7862(02)00030-8, 10.1016/S1472-7862(02)00030-8]
[8]   Orthopalladated phosphinite complexes as high-activity catalysts for the Suzuki reaction [J].
Bedford, RB ;
Hazelwood, SL ;
Horton, PN ;
Hursthouse, MB .
DALTON TRANSACTIONS, 2003, (21) :4164-4174
[9]   Orthopalladated and -platinated bulky triarylphosphite complexes: Synthesis, reactivity and application as high-activity catalysts for Suzuki and Stille coupling reactions [J].
Bedford, RB ;
Hazlewood, SL ;
Limmert, ME ;
Albisson, DA ;
Draper, SM ;
Scully, PN ;
Coles, SJ ;
Hursthouse, MB .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3216-3227
[10]   C2-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki-Miyaura Cross-Coupling [J].
Bermejo, Antonio ;
Ros, Abel ;
Fernandez, Rosario ;
Lassaletta, Jose M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) :15798-+