Palladium-Catalyzed Suzuki Reaction in Aqueous Media

被引:16
作者
Liu, Ning [1 ]
Liu, Chun [1 ]
Jin, Zilin [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
Suzuki reaction; palladium catalyst; aqueous phase; CROSS-COUPLING REACTIONS; MICROWAVE-ASSISTED SUZUKI; N-HETEROCYCLIC CARBENES; LIGAND-FREE PALLADIUM; MIYAURA REACTION; ARYL CHLORIDES; ARYLBORONIC ACIDS; HIGHLY EFFICIENT; RECYCLABLE CATALYST; HECK REACTIONS;
D O I
10.6023/cjoc1109052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed Suzuki cross-coupling reaction has become one of the most powerful tools for sp(2)-sp(2) carbon-carbon bond formation. This coupling reaction is increasingly being applied in the synthesis of pharmaceuticals, natural products and advanced functional materials. In recent years, developing aqueous systems for the Suzuki reaction has attracted attention from many researchers. This paper reviews the recent progress in the Suzuki reaction using neat water and aqueous-organic co-solvent as reaction media. A large number of different strategies for the Suzuki reaction in water have been developed, in which the authors aim at the solutions to the enhancement of the reactivity of the palladium-catalyzed Suzuki reaction using water-soluble ligands, surfactants, microwave assistance, or ligand-free system.
引用
收藏
页码:860 / 876
页数:17
相关论文
共 128 条
[1]   PEG350-based di-(2-pyridyl)methylamine as a ligand in the Pd-catalyzed water Suzuki-Miyaura reaction of aryl chlorides [J].
Adidou, Oluissam ;
Goux-Henry, Catherine ;
Safi, Mohamed ;
Soufiaoui, Mohamed ;
Framery, Eric .
TETRAHEDRON LETTERS, 2008, 49 (50) :7217-7219
[2]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[3]  
Anastas P., 1998, GREEN CHEM THEORY PR
[4]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[5]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[6]   Generation of a small library of highly electron-rich 2-(Hetero)aryl-substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue [J].
Appukkuttan, P ;
Orts, AB ;
Chandran, RP ;
Goeman, JL ;
Van der Eycken, J ;
Dehaen, W ;
Van der Eycken, E .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3277-3285
[7]   Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].
Arvela, RK ;
Leadbeater, NE .
ORGANIC LETTERS, 2005, 7 (11) :2101-2104
[8]   Microwave-promoted Suzuki coupling reactions with organotrifluoroborates in water using ultra-low catalyst loadings [J].
Arvela, RK ;
Leadbeater, NE ;
Mack, TL ;
Kormos, CM .
TETRAHEDRON LETTERS, 2006, 47 (02) :217-220
[9]   Reusable, polymer-supported, palladium-catalyzed, atom-efficient coupling reaction of aryl halides with sodium tetraphenylborate in water by focused microwave irradiation [J].
Bai, Lin ;
Wang, Jin-Xian .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (02) :315-320
[10]   Isolation of an [SNS]Pd(II) pincer with a water ladder and its Suzuki coupling activity in water [J].
Bai, Shi-Qiang ;
Hor, T. S. Andy .
CHEMICAL COMMUNICATIONS, 2008, (27) :3172-3174