Recent advances in Sonogashira reactions

被引:1374
作者
Chinchilla, Rafael [1 ]
Najera, Carmen
机构
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
关键词
CROSS-COUPLING REACTIONS; PD-CATALYZED SONOGASHIRA; ONE-POT SYNTHESIS; PALLADIUM(II) ETHYLENEDIAMINE COMPLEX; IRON/COPPER COCATALYZED ALKYNYLATION; SUPPORTED METAL NANOPARTICLES; NONLINEAR-OPTICAL-PROPERTIES; MIXED AQUEOUS-MEDIUM; 1ST TOTAL-SYNTHESIS; COPPER-FREE;
D O I
10.1039/c1cs15071e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The coupling of aryl or vinyl halides with terminal acetylenes catalysed by palladium and other transition metals, commonly termed as Sonogashira cross-coupling reaction, is one of the most important and widely used sp(2)-sp carbon-carbon bond formation reactions in organic synthesis, frequently employed in the synthesis of natural products, biologically active molecules, heterocycles, molecular electronics, dendrimers and conjugated polymers or nanostructures. This critical review focuses on developments in the Sonogashira reaction achieved in recent years concerning catalysts, reaction conditions and substrates (352 references).
引用
收藏
页码:5084 / 5121
页数:38
相关论文
共 434 条
[1]   Preparation of Ethynylpyridine Macrocycles by Oxidative Coupling of an Ethynylpyridine Trimer with Terminal Acetylenes [J].
Abe, Hajime ;
Kurokawa, Hiroyuki ;
Chida, Yusuke ;
Inouye, Masahiko .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :309-311
[2]   Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts [J].
Akiyama, Y. ;
Meng, X. ;
Fujita, S. ;
Chen, Y. -C. ;
Lu, N. ;
Cheng, H. ;
Zhao, F. ;
Arai, M. .
JOURNAL OF SUPERCRITICAL FLUIDS, 2009, 51 (02) :209-216
[3]   Oxime-derived palladacycles as source of palladium nanoparticles [J].
Alonso, Diego A. ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (08) :2891-2902
[4]   Synthesis of 3-alkynylselenophene derivatives by a copper-free sonogashira cross-coupling reaction [J].
Alves, Diego ;
dos Reis, Joel S. ;
Luchese, Cristiane ;
Nogueira, Cristina W. ;
Zeni, Gilson .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (02) :377-382
[5]   NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].
AMATORE, C ;
BLART, E ;
GENET, JP ;
JUTAND, A ;
LEMAIREAUDOIRE, S ;
SAVIGNAC, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839
[6]   The effect of steric bulk in Sonogashira coupling reactions [J].
an der Heiden, Markus ;
Plenio, Herbert .
CHEMICAL COMMUNICATIONS, 2007, (09) :972-974
[7]   Insights into Sonogashira cross-coupling by high-throughput kinetics and descriptor modeling [J].
an der Heiden, Markus R. ;
Plenio, Herbert ;
Immel, Stefan ;
Burello, Enrico ;
Rothenberg, Gadi ;
Hoefsloot, Huub C. J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (09) :2857-2866
[8]   Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions [J].
Appukkuttan, Prasad ;
Van der Eycken, Erik .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (07) :1133-1155
[9]   Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].
Astruc, Didier .
INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894
[10]   Facile synthesis of palladium nanoclusters and their catalytic activity in Sonogashira coupling reactions [J].
Athilakshmi, J. ;
Ramanathan, S. ;
Chand, Dillip Kumar .
TETRAHEDRON LETTERS, 2008, 49 (36) :5286-5288