A comparative study of hydroxyl- and carboxylate-functionalized imidazolium and benzimidazolium salts as precursors for N-heterocyclic carbene ligands

被引：20
作者：
Allegue, Andres
Albert-Soriano, Maria
Pastor, Isidro M. [1 ]
机构：
[1] Univ Alicante, Dept Organ Chem, Fac Sci, E-03080 Alicante, Spain
来源：
APPLIED ORGANOMETALLIC CHEMISTRY | 2015年 / 29卷 / 09期
关键词：
N-heterocyclic carbenes; imidazolium; benzimidazolium; palladium; Suzuki-Miyaura; ACIDIC IONIC LIQUIDS; COMPLEXES SYNTHESIS; PALLADIUM(II) COMPLEXES; ELECTRONIC-STRUCTURE; NHC-PD(II) COMPLEX; COUPLING REACTIONS; STABLE CARBENES; SYNTHETIC ROUTE; SUZUKI REACTION; NHC;
D O I：
10.1002/aoc.3343
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The preparation of imidazolium and benzimidazolium salts with hydroxyl or carboxylate functions has been achieved using straightforward synthetic pathways. These salts in combination with palladium(II) acetate give active catalytic systems for Suzuki reaction. A comparative study has been performed, which has revealed that both the heterocycle and the functional group are important for the catalytic activity and stability of the catalyst. Copyright (c) 2015 John Wiley & Sons, Ltd.
引用
收藏
页码：624 / 632
页数：9
相关论文
共 104 条
[1]   Optimization of the Mizoroki-Heck reaction using design of experiment (DoE) [J].
Aggarwal, VK ;
Staubitz, AC ;
Owen, M .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (01) :64-69
[2]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].
Alonso, Francisco ;
Beletskaya, Irina P. ;
Yus, Miguel .
TETRAHEDRON, 2008, 64 (14) :3047-3101
[3]   Asymmetric lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes;: crystallographic characterisation and Lewis acid catalysis [J].
Arnold, PL ;
Rodden, M ;
Davis, KM ;
Scarisbrick, AC ;
Blake, AJ ;
Wilson, C .
CHEMICAL COMMUNICATIONS, 2004, (14) :1612-1613
[4]   Chelating alkoxy-N-heterocyclic carbene complexes of silver and copper [J].
Arnold, PL ;
Scarisbrick, AC ;
Blake, AJ ;
Wilson, C .
CHEMICAL COMMUNICATIONS, 2001, (22) :2340-2341
[5]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[6]   Intramolecular Oxidation of the Alcohol Functionalities in Hydroxyalkyl-N-Heterocyclic Carbene Complexes of Iridium and Rhodium [J].
Benitez, Miriam ;
Mas-Marza, Elena ;
Mata, Jose A. ;
Peris, Eduardo .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (37) :10453-10461
[7]   Nickel(II) Benzimidazolin-2-ylidene Complexes with Thioether-Functionalized Side Chains as Catalysts for Suzuki-Miyaura Cross-Coupling [J].
Bernhammer, Jan C. ;
Huynh, Han Vinh .
ORGANOMETALLICS, 2014, 33 (20) :5845-5851
[8]   Pyrazolin-5-ylidene Palladium(II) Complexes: Synthesis, Characterization, and Application in the Direct Arylation of Pentafluorobenzene [J].
Bernhammer, Jan C. ;
Han Vinh Huynh .
ORGANOMETALLICS, 2012, 31 (14) :5121-5130
[9]   N-Heterocyclic Carbene Ligands and Iron: An Effective Association for Catalysis [J].
Bezier, David ;
Sortais, Jean-Baptiste ;
Darcel, Christophe .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) :19-33
[10]   Electronic structure of stable carbenes, silylenes, and germylenes [J].
Boehme, C ;
Frenking, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (08) :2039-2046
12345678910