A recyclable and efficient triazole ligand for the palladium-catalyzed Suzuki-Miyaura and Mizoroki-Heck reactions

被引：20

作者：

Zhu, Yi-Wei ^{[1
]}

Yi, Wen-Bin ^{[1
]}

Cai, Chun ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Peoples R China

来源：

CATALYSIS COMMUNICATIONS | 2011年 / 15卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Fluorous ligand; 1,2,3]-triazole; Palladium; Coupling reactions; F-SPE (fluorous solid-phase extraction); SOLID-PHASE EXTRACTION; COUPLING REACTIONS; COMPLEXES SYNTHESIS; PYRIDINE CATALYST; ARYL CHLORIDES; SONOGASHIRA; BROMIDES;

D O I：

10.1016/j.catcom.2011.08.023

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new fluoroalkylated 1,4-disubstituted [1,2,3]-triazole was prepared and acted as an efficient ligand in the palladium-catalyzed Suzuki-Miyaura coupling reactions of aryl boronic acids and aryl halides (Ar-Br and Ar-Cl) and Mizoroki-Heck reactions of aryl halides and alkenes. All reactions proceeded smoothly to give the desired products in moderate to excellent yields under the optimal conditions. Moreover, the ligand could be easily recovered by fluorous solid-phase extraction with excellent purity and reused with slightly decrease in its activity. Crown Copyright (C) 2011 Published by Elsevier B.V. All rights reserved.

引用

页码：118 / 122

页数：5

共 36 条

[1] 2-furyl phosphines as ligands for transition-metal-mediated organic synthesis [J].

Andersen, NG ;

Keay, BA .

CHEMICAL REVIEWS, 2001, 101 (04) :997-1030

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

Beletskaya, IP ;

Cheprakov, AV .

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

[3] N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions [J].

Broggi, Julie ;

Clavier, Herve ;

Nolan, Steven P. .

ORGANOMETALLICS, 2008, 27 (21) :5525-5531

[4] Monoligated palladium species as catalysts in cross-coupling reactions [J].

Christmann, U ;

Vilar, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374

[5] Thermal allylations of aldehydes with a fluorous allylstannane. Separation of organic and fluorous products by solid phase extraction with fluorous reverse phase silica gel [J].

Curran, DP ;

Hadida, S ;

He, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6714-6715

[6]

Diebolt O., 2008, J CHEM SOC CHEM COMM, P3190, DOI DOI 10.1039/B804695F

[7] Efficient Suzuki-Miyaura coupling of (hetero)aryl chlorides with thiophene- and furanboronic acids in aqueous n-butanol [J].

Fleckenstein, Christoph A. ;

Plenio, Herbert .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3236-3244

[8] 9-fluorenylphosphines for the Pd-catalyzed Sonogashira, Suzuki, and Buchwald-Hartwig coupling reactions in organic solvents and water [J].

Fleckenstein, Christoph A. ;

Plenio, Herbert .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (09) :2701-2716

[9] The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands [J].

Fu, Gregory C. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1555-1564

[10] ARYLATION METHYLATION AND CARBOXYALKYLATION OF OLEFINS BY GROUP 8 METAL DERIVATIVES [J].

HECK, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5518-&

← 1 2 3 4 →