Efficient Palladium-catalyzed Suzuki-Miyaura reactions using phenolic Schiff base ligands under ambient conditions in aqueous media

被引：12

作者：

Zhou, Zhonggao ^{[1
]}

Zhou, Zhenyun ^{[1
]}

Chen, Aichen ^{[1
]}

Zhou, Xiuhua ^{[2
]}

Qi, Qi ^{[1
]}

Xie, Yongrong ^{[1
]}

机构：

[1] Gannan Normal Univ, Coll Chem & Chem Engn, Ganzhou 341000, Peoples R China

[2] Fujian Inspect & Res Inst Product Qual, Fuzhou 35002, Peoples R China

来源：

TRANSITION METAL CHEMISTRY | 2013年 / 38卷 / 04期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; ARYL CHLORIDES; PD(II) COMPLEXES; ORGANOBORANES; OXYGEN; WATER; ACIDS; HECK; SALT;

D O I：

10.1007/s11243-013-9704-x

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The palladium complexes of a series of simple Schiff base ligands with or without phenolic hydroxyl groups have been found to be the excellent catalysts for the Suzuki-Miyaura reactions of aryl iodides, aryl bromides and activated aryl chlorides under ambient conditions in aqueous ethanol media. The introduction of phenolic hydroxyl and/or pyridine groups to the ligands increased the catalytic activity. Under optimal reaction conditions, satisfactory to excellent yields of biaryls were obtained with a wide range of substrates for relatively low loadings of catalyst. Phenolic hydroxyl group and N-4-type Schiff base ligands (L1-2) have been proven to be the excellent catalysts for the Suzuki-Miyaura reactions of aryl iodides, aryl bromides and activated aryl chlorides in aqueous ethanol under ambient. Furthermore, a diverse choice of functionalized arylboronic acids bearing difluoro, trifluoro and trifluoromethyl substituents were successfully coupled (> 97 %).

引用

页码：401 / 405

页数：5

共 36 条

[11] Palladium nanoparticles supported on polyaniline nanofibers as a semi-heterogeneous catalyst in water [J].

Gallon, Benjamin J. ;

Kojima, Robert W. ;

Kaner, Richard B. ;

Diaconescu, Paula L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) :7251-7254

[12] Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems [J].

Grasa, GA ;

Viciu, MS ;

Huang, JK ;

Zhang, CM ;

Trudell, ML ;

Nolan, SP .

ORGANOMETALLICS, 2002, 21 (14) :2866-2873

[13] 1,1′-Binaphthyldiamine-Based Lewis Bases as Readily Available and Efficient Organocatalysts for the Reduction of N-Aryl and N-Alkyl Ketimines [J].

Guizzetti, Stefania ;

Benaglia, Maurizio ;

Celentano, Giuseppe .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) :3683-3687

[14] Catalytic activities of Schiff base transition metal complexes [J].

Gupta, K. C. ;

Sutar, Alekha Kumar .

COORDINATION CHEMISTRY REVIEWS, 2008, 252 (12-14) :1420-1450

[15] Polymer-supported macrocyclic Schiff base palladium complex: An efficient and reusable catalyst for Suzuki cross-coupling reaction under ambient condition [J].

He, Ying ;

Cai, Chun .

CATALYSIS COMMUNICATIONS, 2011, 12 (07) :678-683

[16] A Reusable Polymer-Anchored Palladium(II) Schiff Base Complex Catalyst for the Suzuki Cross-Coupling, Heck and Cyanation Reactions [J].

Islam, S. M. ;

Mondal, P. ;

Tuhina, K. ;

Roy, A. S. ;

Mondal, S. ;

Hossain, D. .

JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2010, 20 (02) :264-277

[17] A novel ionic liquid-supported Schiff base ligand applied in the Pd-catalyzed Suzuki-Miyaura coupling reaction [J].

Li, Bin ;

Li, Yi-Qun ;

Zheng, Jia .

ARKIVOC, 2010, :163-170

[18]

Littke AF, 1998, ANGEW CHEM INT EDIT, V37, P3387, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO

[19]

2-P

[20] Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki-Miyaura coupling catalysts [J].

Mahamo, Tebello ;

Mogorosi, Mokgolela M. ;

Moss, John R. ;

Mapolie, Selwyn F. ;

Slootweg, J. Chris ;

Lammertsma, Koop ;

Smith, Gregory S. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 703 :34-42

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