A comparative homocoupling reaction of aryl halides using monomeric orthopalladated complex of 4-methoxybenzoylmethylenetriphenylphosphorane under conventional and microwave irradiation conditions

被引:19
作者
Hajipour, Abdol R. [1 ,2 ]
Karami, Kazem [1 ]
Tavakoli, Ghazal [1 ]
机构
[1] Isfahan Univ Technol, Dept Chem, Pharmaceut Res Lab, Esfahan 84156, Iran
[2] Univ Wisconsin, Sch Med, Dept Pharmacol, Madison, WI 53706 USA
关键词
homocoupling; catalyst; palladacycle; microwaves; CROSS-COUPLING REACTIONS; SYMMETRICAL BIARYLS; ULLMANN SYNTHESIS; SELECTIVE AGENT; BOND FORMATION; PALLADIUM; CONVENIENT; CHEMISTRY; CATALYSTS; IODIDES;
D O I
10.1002/aoc.1804
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The activity of [Pd(C6H4CH2NH2-kappa(2)-C-N)PPh3MOBPPY]OTf complex, A (MOBPPY = 4-methoxybenzoylmethylenetriphenylphosphoraneylide) was investigated in the homocoupling reaction of a vast range of aryl halides under both conventional and microwave irradiation conditions and their results were compared. The complex was active and showed high efficiency in the formation of new C-C bonds. The yields were excellent using a catalytic amount of [Pd(C6H4CH2NH2-kappa(2)-C-N)PPh3MOBPPY]OTf complex in N, N-dimethylformamide at 120 degrees C. In comparison to conventional heating conditions, the reactions under microwave irradiation gave higher yields in shorter reaction times. Copyright (C) 2011 John Wiley & Sons, Ltd.
引用
收藏
页码:567 / 576
页数:10
相关论文
共 74 条
[1]   Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex [J].
Adamo, Carlo ;
Amatore, Christian ;
Ciofini, Ilaria ;
Jutand, Anny ;
Lakmini, Hakim .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6829-6836
[2]   PALLADIUM-CATALYZED OXIDATIONS IN SELECTIVE ORGANIC-SYNTHESIS [J].
BACKVALL, JE .
PURE AND APPLIED CHEMISTRY, 1983, 55 (11) :1669-1676
[3]  
Beller M., 1998, TRANSITION METALS OR
[4]   Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A [J].
Brimble, MA ;
Lai, MYH .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (12) :2084-2095
[5]   Enantio- and Diastereoselective Chemoenzymatic Synthesis of C2-Symmetric Biaryl-Containing Diols [J].
Burda, Edyta ;
Bauer, Walter ;
Hummel, Werner ;
Groeger, Harald .
CHEMCATCHEM, 2010, 2 (01) :67-72
[6]   DEVELOPMENT AND APPLICATION OF A CONTINUOUS MICROWAVE REACTOR FOR ORGANIC-SYNTHESIS [J].
CABLEWSKI, T ;
FAUX, AF ;
STRAUSS, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3408-3412
[7]   Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity [J].
Carrettin, S ;
Guzman, J ;
Corma, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2242-2245
[8]   HOST-GUEST COMPLEXATION .21. CATALYSIS AND CHIRAL RECOGNITION THROUGH DESIGNED COMPLEXATION OF TRANSITION-STATES IN TRANSACYLATIONS OF AMINO ESTER SALTS [J].
CHAO, Y ;
WEISMAN, GR ;
SOGAH, GDY ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4948-4958
[9]  
CINTAS P, 1995, SYNLETT, P1087
[10]  
Collman J.P., 1987, PRINCIPLES APPL ORGA