Homeopathic ligand-free palladium as a catalyst in the Heck reaction. A comparison with a palladacycle

被引：534
作者：
de Vries, AHM [1 ]
Mulders, JMCA [1 ]
Mommers, JHM [1 ]
Henderickx, HJW [1 ]
de Vries, JG [1 ]
机构：
[1] DSM Pharma Chem Adv Synth, Catalysis & Dev, NL-6160 MD Geleen, Netherlands
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 18期
关键词：
D O I：
10.1021/ol035184b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Ligand-free Pd(OAc)(2) can be used as a catalyst in the Heck reaction of aryl bromides as long as the amount of catalyst is kept between 0.01 and 0.1 mol %. At higher concentrations palladium black forms and the reaction stops. The actual catalyst is monomeric. Palladacycles merely serve as a source of ligand-free palladium in Heck reactions of aryl bromides.
引用
收藏
页码：3285 / 3288
页数：4
相关论文
共 61 条
[51]  
Reetz MT, 2000, ANGEW CHEM INT EDIT, V39, P165, DOI 10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO
[52]  
2-B
[53]   Thermomorphic fluorous imine and thioether palladacycles as precursors for highly active Heck and Suzuki catalysts; evidence for palladium nanoparticle pathways [J].
Rocaboy, C ;
Gladysz, JA .
NEW JOURNAL OF CHEMISTRY, 2003, 27 (01) :39-49
[54]   Highly active thermomorphic fluorous palladacycle catalyst precursors for the Heck reaction; Evidence for a palladium nanoparticle pathway [J].
Rocaboy, C ;
Gladysz, JA .
ORGANIC LETTERS, 2002, 4 (12) :1993-1996
[55]   Kinetic studies of Heck coupling reactions using palladacycle catalysts: Experimental and kinetic modeling of the role of dimer species [J].
Rosner, T ;
Le Bars, J ;
Pfaltz, A ;
Blackmond, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :1848-1855
[56]  
Stephan MS, 1998, ANGEW CHEM INT EDIT, V37, P662, DOI 10.1002/(SICI)1521-3773(19980316)37:5<662::AID-ANIE662>3.0.CO
[57]  
2-0
[58]  
STEPHAN MS, 2000, CHEM IND, V82, P379
[59]  
van Strijdonck GPF, 1999, EUR J INORG CHEM, P1073
[60]   Advances in the Heck chemistry of aryl bromides and chlorides [J].
Whitcombe, NJ ;
Hii, KK ;
Gibson, SE .
TETRAHEDRON, 2001, 57 (35) :7449-7476
1234567