Efficient and copper-free Sonogashira cross-coupling reaction catalyzed by Pd(OAc)2/pyrimidines catalytic system

被引：68

作者：

Li, JH ^{[1
]}

Zhang, XD ^{[1
]}

Xie, YX ^{[1
]}

机构：

[1] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Chem Biol & Tradit Cinese Med Res, Changsha 410081, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 20期

关键词：

palladium; cross-coupling reaction; homogeneous catalysis;

D O I：

10.1002/ejoc.200500519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and copper-free catalyst system for Sonogashira cross-coupling reaction is presented. In the presence of 3 mol-% of Pd(OAC)(2) and 6 mol-% of 2-aminopyrimidine-4,6-diol, various aryl iodides and bromides can be coupled smoothly with terminal alkynes to afford the corresponding coupled alkynes in moderate to excellent yields under mild conditions. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

引用

收藏

页码：4256 / 4259

页数：4

相关论文

共 46 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] 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

[3] Synthetic applications of oxime-derived palladacycles as versatile catalysts in cross-coupling reactions [J].

Alonso, DA ;

Botella, L ;

Nájera, C ;

Pacheco, C .

SYNTHESIS-STUTTGART, 2004, (10) :1713-1718

[4] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

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

Arques, A ;

Auñon, D ;

Molina, P .

TETRAHEDRON LETTERS, 2004, 45 (22) :4337-4340

[6] 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

[7]

Bohlmann F, 1973, NATURALLY OCCURRING

[8]

Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO

[9]

2-X

[10] A copper- and amine-free sonogashira reaction employing aminophosphines as ligands [J].

Cheng, J ;

Sun, YH ;

Wang, F ;

Guo, MJ ;

Xu, JH ;

Pan, Y ;

Zhang, ZG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5428-5432

← 1 2 3 4 5 →