A copper- and amine-free Sonogashira coupling reaction promoted by a ferrocene-based phosphinimine-phosphine ligand at low catalyst loading

被引:89
作者
Arques, A [1 ]
Auñon, D [1 ]
Molina, P [1 ]
机构
[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30071 Murcia, Spain
关键词
Sonogashira reaction; copper-free; palladium; catalysis; alkynes;
D O I
10.1016/j.tetlet.2004.03.194
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium(II) complex containing a ferrocene-based phosphinimine-phosphine ligand was applied to the amine- and copper-free Sonogashira coupling of aryl iodides and aryl bromides with terminal alkynes using 1 equiv of tetrabutyl ammonium acetate as an activator. The corresponding disubstituted alkynes were obtained in high yields and TONs using 0.1 mol% Pd-catalyst. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4337 / 4340
页数:4
相关论文
共 36 条
[1]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].
ALAMI, M ;
FERRI, F ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406
[2]   A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368
[3]  
Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO
[4]  
2-X
[5]   Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].
Bunz, UHF .
CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644
[6]   Phosphoraneiminato complexes of transition metals [J].
Dehnicke, K ;
Krieger, M ;
Massa, W .
COORDINATION CHEMISTRY REVIEWS, 1999, 182 :19-65
[7]   Sonogashira cross-coupling reactions catalysed by heterogeneous copper-free Pd-zeolites [J].
Djakovitch, L ;
Rollet, P .
TETRAHEDRON LETTERS, 2004, 45 (07) :1367-1370
[8]   Phosphine-pyridyl and related ligands in synthesis and catalysis [J].
Espinet, P ;
Soulantica, K .
COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 :499-556
[9]   A copper-free palladium catalyzed cross coupling reaction of vinyl tosylates with terminal acetylenes [J].
Fu, XY ;
Zhang, SY ;
Yin, JG ;
Schumacher, DP .
TETRAHEDRON LETTERS, 2002, 43 (37) :6673-6676
[10]   A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling [J].
Fukuyama, T ;
Shinmen, M ;
Nishitani, S ;
Sato, M ;
Ryu, I .
ORGANIC LETTERS, 2002, 4 (10) :1691-1694