Palladium catalysts for highly selective Sonogashira reactions of aryl and heteroaryl bromides

被引：47

作者：

Torborg, Christian ^{[1
]}

Zapf, Alexander ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

CHEMSUSCHEM | 2008年 / 1卷 / 1-2期

关键词：

alkynes; heterocycles; homogeneous catalysis; palladium; phosphanes;

D O I：

10.1002/cssc.200700004

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium catalysts have been studied for the Sonogashira-Hagihara coupling of aryl and heteroaryl bromides with terminal alkynes. Among the different biarylphosphines tested, 2-(di-tert-butylphosphino)-N-phenylindole (cataCXium Plntb) allows the efficient coupling of both activated and deactivated (hetero)aryl bromides in the presence of sodium tetrachloropalladate in tetramethylethylenediamine (TMEDA) at 80 degrees C. The catalyst system gives high turnover numbers (up to 14 100) and shows a broad tolerance towards functional groups such as OH and NH2, as well as heterocycles.

引用

页码：91 / 96

页数：6

共 81 条

[1] Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives [J].

Ahmed, MSM ;

Mori, A .

TETRAHEDRON, 2004, 60 (44) :9977-9982

[2] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[3]

[Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22

[4]

[Anonymous], 2002, J ORGANOMET CHEM

[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] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[7]

Beller M, 1998, EUR J INORG CHEM, P29

[8] First efficient palladium-catalyzed Heck reactions of aryl bromides with alkyl methacrylate [J].

Beller, M ;

Riermeier, TH .

TETRAHEDRON LETTERS, 1996, 37 (36) :6535-6538

[9] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS [J].

BELLER, M ;

FISCHER, H ;

HERRMANN, WA ;

OFELE, K ;

BROSSMER, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1848-1849

[10]

Beller M., 1995, ANGEW CHEM, V107, P1992

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