Palladium nano-particles supported on agarose as efficient catalyst and bioorganic ligand for C-C bond formation via solventless Mizoroki-Heck reaction and Sonogashira-Hagihara reaction in polyethylene glycol (PEG 400)

被引：91

作者：

Firouzabadi, Habib ^{[1
]}

Iranpoor, Nasser ^{[1
]}

Kazemi, Faezeh ^{[1
]}

Gholinejad, Mohammad ^{[1
,2
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

[2] IASBS, Dept Chem, Gava Zang, Zanjan, Iran

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2012年 / 357卷

关键词：

Agarose; Mizoroki-Heck; Sonogashira-Hagihara; Nanoparticle; Palladium; Polyethylene glycol; Copper-free; CROSS-COUPLING REACTION; N-HETEROCYCLIC CARBENE; TERMINAL ALKYNES; NANOPARTICLES; SILICA; WATER; HALIDES; ABSENCE; BULKY;

D O I：

10.1016/j.molcata.2012.02.006

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：

In this study, abundant naturally occurring agarose has been used as a support and ligand for palladium nanoparticles. In the presence of this catalytic system, Mizoroki-Heck and Sonogashira-Hagihara coupling reactions were performed successfully. The catalyst exhibits high activity in Mizoroki-Heck reaction under phosphane and solvent-free conditions for the reaction of iodo- and bromoarenes with butyl acrylate and styrene. This catalytic system also showed high catalytic activity for Sonogashira-Hagihara coupling reaction of various aryl halides (I, Br, Cl) under copper and ligand-free conditions in polyethylene glycol (PEG 400) as an ecofriendly and non-poisonous media. The catalyst can be separated from the reaction mixture and reused for the similar batches of the reaction. High efficiency of the catalyst along with its recycling ability and the rather low Pd-loading which are demonstrated in both Mizoroki-Heck and Sonogashira-Hagihara reactions are the merits of the presented catalyst system. (C) 2012 Published by Elsevier B.V.

引用

页码：154 / 161

页数：8

共 57 条

[31] An imidazolium-based phosphinite ionic liquid (IL-OPPh2) as a reusable reaction medium and PdII ligand in Heck reactions of aryl halides with styrene and n-butyl acrylate [J].

Iranpoor, Nasser ;

Firouzabadi, Habib ;

Azadi, Roya .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (13) :2197-2201

[32] New N-heterocyclic carbene palladium complex/ionic liquid matrix immobilized on silica: Application as recoverable catalyst for the Heck reaction [J].

Karimi, B ;

Enders, D .

ORGANIC LETTERS, 2006, 8 (06) :1237-1240

[33]

Karimi B., 2010, ORG SYNTH, V7, P643

[34]

Karimi B., 2010, Synthesis, V9, P1399

[35] Immobilized palladium nanoparticles on a silica-starch substrate (PNP-SSS): as an efficient heterogeneous catalyst for Heck and copper-free Sonogashira reactions in water [J].

Khalafi-Nezhad, Ali ;

Panahi, Farhad .

GREEN CHEMISTRY, 2011, 13 (09) :2408-2415

[36] Solvent-free, open-vessel microwave-promoted Heck couplings: From the mmol to the mol scale [J].

Leadbeater, Nicholas E. ;

Williams, Victoria A. ;

Barnard, Thomas M. ;

Collins, Michael J., Jr. .

SYNLETT, 2006, (18) :2953-2958

[37] Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions [J].

Li, JH ;

Liang, Y ;

Xie, YX .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4393-4396

[38] Asymmetric transfer hydrogenation using recoverable ruthenium catalyst immobilized into magnetic mesoporous silica [J].

Li, Jun ;

Zhang, Yanmei ;

Han, Difei ;

Gao, Qiang ;

Li, Can .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2009, 298 (1-2) :31-35

[39]

Link J.T., 2002, ORG REACT, V60, P157

[40] Toward green catalytic synthesis - Transition metal-catalyzed reactions in non-conventional media [J].

Liu, Shifang ;

Xiao, Jianliang .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 270 (1-2) :1-43

← 1 2 3 4 5 6 →