Highly Active Palladium Catalyst for the Sonogashira Coupling Reaction of Unreactive Aryl Chlorides

被引:26
作者
Lee, Dong-Hwan [1 ]
Kwon, Young-Jun [1 ]
Jin, Myung-Jong [1 ]
机构
[1] Inha Univ, Dept Chem Engn, Inchon 402751, South Korea
基金
新加坡国家研究基金会;
关键词
aryl chlorides; cross-coupling; homogeneous catalysts; palladium; phosphane ligands; Sonogashira reaction; PINCER COMPLEXES; FACILE SYNTHESIS; SUZUKI-MIYAURA; EFFICIENT; ALKYNES; DERIVATIVES; CONVENIENT; ARYLATION; BROMIDES; LIGANDS;
D O I
10.1002/adsc.201100747
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This communication reports on the beta-diketiminatophosphane palladium-catalyzed copper-free Sonogashira coupling of aryl chlorides with alkynes. A catalyst loading of 0.5 mol% is sufficient to achieve high performance under relatively mild reaction conditions. Furthermore, dialkynylbenzenes are efficiently prepared by one-pot double Sonogashira couplings of aryl dichlorides
引用
收藏
页码:3090 / 3094
页数:5
相关论文
共 53 条
[1]   Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].
Adjabeng, G ;
Brenstrum, T ;
Frampton, CS ;
Robertson, AJ ;
Hillhouse, J ;
McNulty, J ;
Capretta, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5082-5086
[2]   C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158
[3]   The effect of steric bulk in Sonogashira coupling reactions [J].
an der Heiden, Markus ;
Plenio, Herbert .
CHEMICAL COMMUNICATIONS, 2007, (09) :972-974
[4]  
Anderson K.W., 2005, ANGEW CHEMIE, V117, P6329, DOI DOI 10.1002/ANGE.200502017
[5]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[6]  
[Anonymous], 2004, METAL CATALYZED CROS
[7]   Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II):: Application to Sonogashira cross-coupling reactions [J].
Batey, RA ;
Shen, M ;
Lough, AJ .
ORGANIC LETTERS, 2002, 4 (09) :1411-1414
[8]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[9]   Highly Convenient, Clean, Fast, and Reliable Sonogashira Coupling Reactions Promoted by Aminophosphine-Based Pincer Complexes of Palladium Performed under Additive-and Amine-Free Reaction Conditions [J].
Bolliger, Jeanne L. ;
Frech, Christian M. .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) :891-902
[10]   Polyethynylated cyclic π-systems:: scaffoldings for novel two and three-dimensional carbon networks [J].
Bunz, UHF ;
Rubin, Y ;
Tobe, Y .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (02) :107-119