Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction

被引:32
作者
Hajipour, Abdol R. [1 ,2 ]
Rafiee, Fatemeh [1 ]
机构
[1] Isfahan Univ Technol, Pharmaceut Res Lab, Dept Chem, Esfahan 84156, Iran
[2] Univ Wisconsin, Dept Pharmacol, Sch Med, Madison, WI 53706 USA
关键词
Cyclopalladated complex; Catalyst; Tribenzylamine; Heck reaction; N-HETEROCYCLIC CARBENE; PHOSPHA-PALLADACYCLES; PALLADIUM COMPLEXES; ARYL CHLORIDES; CYCLOMETALATED COMPLEXES; MICROWAVE IRRADIATION; INTERNAL METALATION; MOLECULAR-STRUCTURE; ORGANIC-SYNTHESIS; CRYSTAL-STRUCTURE;
D O I
10.1016/j.jorganchem.2011.03.023
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The activity of [Pd{C6H4(CH2N(CH2Ph)(2))} (mu-Br)](2) complex was investigated in the HeckeMizoroki C-C cross-coupling reaction. This complex is an active and efficient catalyst for the Heck reaction of aryl iodides, bromides and even chlorides and also arenesulfonyl chlorides. The cross-coupled products were produced in excellent yields in short reaction time using a catalytic amount of [Pd{C6H4(CH2N(CH2Ph)(2)) (mu-Br)](2) complex in NMP at 130 degrees C. (C) 2011 Elsevier B. V. All rights reserved.
引用
收藏
页码:2669 / 2675
页数:7
相关论文
共 72 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]   STRUCTURAL STUDIES OF STERIC EFFECTS IN PHOSPHINE COMPLEXES .4. SYNTHESIS AND CRYSTAL AND MOLECULAR-STRUCTURE OF TRANS-DI-IODOBIS(TRI-ORTHO-TOLYLPHOSPHINE)PLATINUM(II)-DICHLOROMETHANE(1-1) [J].
ALYEA, EC ;
DIAS, SA ;
FERGUSON, G ;
ROBERTS, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1979, (06) :948-951
[3]   CRYSTAL AND MOLECULAR-STRUCTURES OF BIS(MU-CHLORO)BIS[0-(DIMESITYLPHOSPHINO)-3,5-DIMETHYLBENZYL]-DIPALLADIUM(II) ACETONE SOLVATE, [PD(P(MES)2C6H2(CH3)2CH2)CL]2.2(CH3COCH3), AND ITS PLATINUM ANALOG [PT(P(MES)2C6H2(CH3)2CH2)CL]2.2(CH3COCH3) - CYCLOMETALATED COMPLEXES OF THE BULKIEST KNOWN PHOSPHINE TRIMESITYLPHOSPHINEC [J].
ALYEA, EC ;
FERGUSON, G ;
MALITO, J ;
RUHL, BL .
ORGANOMETALLICS, 1989, 8 (05) :1188-1191
[4]  
[Anonymous], METAL CATALYZED CROS
[5]   Synthesis, characterization and X-ray crystal structure determination of cyclopalladated [Csp2,N,N′]-, zwitterionic and chelated compounds in the reaction of 3,5-diphenyl-N-alkylaminopyrazole derived ligands with Pd(II) [J].
Aragay, Gemma ;
Pons, Josefina ;
Garcia-Anton, Jordi ;
Solans, Xavier ;
Font-Bardia, Merce ;
Ros, Josep .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (21-22) :3396-3404
[6]  
Bader RR, 1996, CHIMIA, V50, P99
[7]   The influence of steric bulk on the geometry of triarylphosphite-based palladacycles and their tricyclohexylphosphine adducts [J].
Bedford, RB ;
Betham, M ;
Coles, SJ ;
Horton, PN ;
López-Sáez, MJ .
POLYHEDRON, 2006, 25 (04) :1003-1010
[8]   N-Heterocyclic carbene adducts of orthopalladated triarylphosphite complexes [J].
Bedford, RB ;
Betham, M ;
Blake, ME ;
Frost, RM ;
Horton, PN ;
Hursthouse, MB ;
López-Nicolás, RM .
DALTON TRANSACTIONS, 2005, (16) :2774-2779
[9]   Catalytic intermolecular ortho-arylation of phenols [J].
Bedford, RB ;
Limmert, ME .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8669-8682
[10]   Intramolecular direct arylation in the synthesis of fluorinated carbazoles [J].
Bedford, Robin B. ;
Betham, Michael ;
Charmant, Jonathan P. H. ;
Weeks, Amanda L. .
TETRAHEDRON, 2008, 64 (26) :6038-6050