Heck Cross-Coupling of Aryldiazonium Tetrafluoroborate with Acrylates Catalyzed by Palladium on Charcoal

被引:83
作者
Felpin, Francois-Xavier [1 ]
Fouquet, Eric [1 ]
Zakri, Cecile [2 ]
机构
[1] Univ Bordeaux, CNRS, Inst Mol Sci, F-33405 Talence, France
[2] Univ Bordeaux, Ctr Rech Paul Pascal, CNRS, F-33600 Pessac, France
关键词
acrylates; aryldiazonium tetrafluoroborate salts; Heck reaction; palladium on charcoal; practical cross-coupling;
D O I
10.1002/adsc.200800539
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A property-activity relationship study of various palladium supported on charcoal (Pd/C) catalysts has been undertaken for the Heck reaction of aryldiazonium tetrafluoroborate with acrylates. The optimized protocol enables the cross-coupling with a low loading of palladium at room temperature in technical grade methanol. Although the catalyst could not be recycled at this time, measurement of the palladium content by inductively coupled plasma mass spectrometry (ICP-MS) shows low palladium contamination of the solvent and product, rendering this method safer for the environment compared to homogeneous conditions.
引用
收藏
页码:2559 / 2565
页数:7
相关论文
共 57 条
[1]   Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions [J].
Artuso, E ;
Barbero, M ;
Degani, I ;
Dughera, S ;
Fochi, R .
TETRAHEDRON, 2006, 62 (13) :3146-3157
[2]  
Baumeister P, 1997, CHIMIA, V51, P144
[3]  
BELLER M, 1995, SYNLETT, P441
[4]   Industrial R&D on catalytic C-C and C-N coupling reactions: A personal account on goals, approaches and results [J].
Blaser, HU ;
Indolese, A ;
Naud, F ;
Nettekoven, U ;
Schnyder, A .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1583-1598
[5]   Application of a new combination of palladium and CaCO3 for an aerobic heck reaction using arenediazonium-salts [J].
Brunner, H ;
de Courcy, NLC ;
Genêt, JP .
TETRAHEDRON LETTERS, 1999, 40 (26) :4815-4818
[6]  
Brunner H, 2000, SYNLETT, P201
[7]   Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: Synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and polycitrin A [J].
Burtoloso, Antonio Carlos B. ;
Garcia, Ariel L. L. ;
Miranda, Karen C. ;
Correia, Carlos Roque D. .
SYNLETT, 2006, (18) :3145-3149
[8]   Ligand-free Stille cross-coupling reaction using Pd/CaCO3 as catalyst reservoir [J].
Coelho, Aline V. ;
de Souza, Andrea Luzia F. ;
de Lima, Paulo G. ;
Wardell, James L. ;
Antunes, O. A. C. .
TETRAHEDRON LETTERS, 2007, 48 (43) :7671-7674
[9]  
Darses S, 2001, EUR J ORG CHEM, V2001, P1121
[10]  
de Vries AHM, 2002, ADV SYNTH CATAL, V344, P996, DOI 10.1002/1615-4169(200210)344:9<996::AID-ADSC996>3.0.CO