Palladium-Nanoparticle-Catalysed Ullmann Reactions in Ionic Liquids with Aldehydes as the Reductants: Scope and Mechanism

被引:65
作者
Calo, Vincenzo [1 ]
Nacci, Angelo [1 ]
Monopoli, Antonio [1 ]
Cotugno, Pietro [1 ]
机构
[1] Univ Bari, Dept Chem, CNR, ICCOM, I-70126 Bari, Italy
关键词
biaryls; ionic liquids; nanoparticles; palladium; Ullmann reactions; CARBON BOND FORMATION; ARYL HALIDES; COUPLING REACTIONS; ASYMMETRIC CATALYSIS; PROCESS OPTIMIZATION; ALPHA-ARYLATION; WATER; BROMIDES; BIARYLS; ZINC;
D O I
10.1002/chem.200801621
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient Ullmann-type reductive homocoupling of aryl, vinyl and heteroaryl halides can be promoted by an aldehyde in tetraalkylammonium ionic liquids under very mild reaction conditions. This simple procedure generates symmetrical biaryls under relatively mild conditions. The ionic liquid is crucial for this process because it behaves simultaneously as a base, ligand and reaction medium. The role of the aldehyde is also discussed and a general mechanism for this unusual reaction is proposed. These results open the way to a new efficient method of Pd-catalysed dehydrogenation of carbonyl compounds.
引用
收藏
页码:1272 / 1279
页数:8
相关论文
共 66 条
[1]   Facile synthesis of symmetrical functionalized biaryls from aryl halides catalyzed by commercial zinc dust using ammonium formate [J].
Abiraj, K ;
Srinivasa, GR ;
Gowda, DC .
TETRAHEDRON LETTERS, 2004, 45 (10) :2081-2084
[2]  
ADAM W, 1983, CHEM FUNCTIONAL GROU
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   Oxidative addition of aryl halides to transient anionic sigma-aryl-palladium(0) intermediates - Application to palladium-catalyzed reductive coupling of aryl halides [J].
Amatore, C ;
Carre, E ;
Jutand, A ;
Tanaka, H ;
Ren, QH ;
Torii, S .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (08) :957-966
[5]   A novel route to the fluorinated diimines: carbon monoxide-promoted reductive homocoupling of fluorinated imidoyl iodides in the presence of a palladium catalyst [J].
Amii, H ;
Kohda, M ;
Seo, M ;
Uneyama, K .
CHEMICAL COMMUNICATIONS, 2003, (14) :1752-1753
[6]  
[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1002/ANGE.200703009
[7]   Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].
Baudoin, O ;
Cesario, M ;
Guénard, D ;
Guéritte, F .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207
[8]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[9]   Solution phase combinatorial synthesis of biaryl libraries employing heterogeneous conditions for catalysis and isolation with size exclusion chromatography for purification [J].
Boger, DL ;
Goldberg, J ;
Andersson, CM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2422-2427
[10]  
Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1