Dichloro[(2-dimethylamino)propyldiphenylphosphine]palladium(II) (PdCl2(alaphos)):: An efficient catalyst for cross-coupling of aryl triflates with alkynyl Grignard reagents

被引:43
作者
Kamikawa, T [1 ]
Hayashi, T [1 ]
机构
[1] Kyoto Univ, Fac Sci, Dept Chem, Kyoto 60601, Japan
关键词
D O I
10.1021/jo981191f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dichloro[(2-dimethylamino)propyldiphenylphosphine]palladium (PdCl2(alaphos)) was found to be much more effective as catalyst than other palladium complexes for cross-coupling of aryl triflates with alkynyl Grignard reagents. Reaction of bromoaryl triflates with alkynyl Grignard reagents in the presence of PdCl2(alaphos) catalyst gave high yields of alkynyl arene bromides, which were formed by selective replacement of triflate by alkynyl group.
引用
收藏
页码:8922 / 8925
页数:4
相关论文
共 25 条
[1]   Stereoselective addition of diphenylphosphine to substituted diphenylethynes: synthetic, NMR and X-ray crystallographic studies [J].
Bookham, JL ;
Smithies, DM ;
Wright, A ;
Thornton-Pett, M ;
McFarlane, W .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (05) :811-818
[2]   PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES - SYNTHESIS OF ARENECARBOXYLIC ACID-DERIVATIVES FROM PHENOLS [J].
CACCHI, S ;
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1986, 27 (33) :3931-3934
[3]   PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486
[4]   Versatile synthetic route to and DSC analysis of dehydrobenzoannulenes: Crystal structure of a heretofore inaccessible [20]annulene derivative [J].
Haley, MM ;
Bell, ML ;
English, JJ ;
Johnson, CA ;
Weakley, TJR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2956-2957
[5]   CHIRAL (BETA-AMINOALKYL)PHOSPHINES - HIGHLY EFFICIENT PHOSPHINE-LIGANDS FOR CATALYTIC ASYMMETRIC GRIGNARD CROSS-COUPLING [J].
HAYASHI, T ;
KONISHI, M ;
FUKUSHIMA, M ;
KANEHIRA, K ;
HIOKI, T ;
KUMADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) :2195-2202
[6]   CATALYTIC ASYMMETRIC-SYNTHESIS OF AXIALLY CHIRAL BIARYLS BY PALLADIUM-CATALYZED ENANTIOPOSITION-SELECTIVE CROSS-COUPLING [J].
HAYASHI, T ;
NIIZUMA, S ;
KAMIKAWA, T ;
SUZUKI, N ;
UOZUMI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9101-9102
[7]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[8]  
HELLWINKEL D, 1989, CHEM BER, V122, P2315
[9]   RATE AND MECHANISM OF OXIDATIVE ADDITION OF ARYL TRIFLATES TO ZEROVALENT PALLADIUM COMPLEXES - EVIDENCE FOR THE FORMATION OF CATIONIC (SIGMA-ARYL)PALLADIUM COMPLEXES [J].
JUTAND, A ;
MOSLEH, A .
ORGANOMETALLICS, 1995, 14 (04) :1810-1817
[10]  
Kamikawa T, 1997, SYNLETT, P163