The [(E,E,E)-1,6,11-tris(p-toluenesulfonyl)-1,6,11-triazacyclopentadeca-3,18,13-triene]Pd(0) complex in the hydroarylation of alkynes in ionic liquids.: An approach to quinolines

被引:45
作者
Cacchi, S
Fabrizi, G
Goggiamani, A
Moreno-Mañas, M
Vallribera, A
机构
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biol At, Sostanze Biol Att, I-00185 Rome, Italy
[2] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain
关键词
hydroarylation; palladium; macrocyclic ligands; ionic liquids; quinolines;
D O I
10.1016/S0040-4039(02)01120-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hydroarylation of alkynes can be successfully conducted in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmin]BF4) in the presence of the [(E,E,E)-1,6,11-tris(p-toluenesulfonyl)-1,6.11-triacyclopentadeca-3 8,13-triene]Pd(0) complex. The catalytic ionic Solution can be recycled for reuse in subsequent reaction runs. The procedure has been applied to the preparation of 3-arylquinolines through a domino hydroarylation/cyclization process. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5537 / 5540
页数:4
相关论文
共 70 条
[1]   CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS [J].
AMORESE, A ;
ARCADI, A ;
BERNOCCHI, E ;
CACCHI, S ;
CERRINI, S ;
FEDELI, W ;
ORTAR, G .
TETRAHEDRON, 1989, 45 (03) :813-828
[2]  
Arcadi A, 1999, EUR J ORG CHEM, V1999, P3305, DOI 10.1002/(SICI)1099-0690(199912)1999:12<3305::AID-EJOC3305>3.0.CO
[3]  
2-O
[4]  
Arcadi A, 2000, EUR J ORG CHEM, V2000, P4099, DOI 10.1002/1099-0690(200012)2000:24<4099::AID-EJOC4099>3.0.CO
[5]  
2-N
[6]   PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO ARYL AND ALKYLETHYNYLSILANES - A STEREO AND REGIOSELECTIVE ROUTE TO FUNCTIONALIZED 2,2-DISUBSTITUTED VINYLSILANES [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F .
TETRAHEDRON LETTERS, 1986, 27 (52) :6397-6400
[7]   THE REACTION OF ARYL IODIDES WITH HINDERED ALPHA,BETA,GAMMA,DELTA-DIENONES IN THE PRESENCE OF THE [PD(OAC)2(PPH3)2]-TRIALKYLAMMONIUM FORMATE REAGENT [J].
ARCADI, A ;
MARINELLI, F ;
CACCHI, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 312 (02) :C27-C32
[8]   PALLADIUM-CATALYZED PREPARATION OF EXO-ARYL DERIVATIVES OF THE NORBORNANE SKELETON [J].
ARCADI, A ;
MARINELLI, F ;
BERNOCCHI, E ;
CACCHI, S ;
ORTAR, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) :249-256
[9]   PALLADIUM-CATALYZED STEREOSELECTIVE HYDROVINYLATION OF DISUBSTITUTED ACETYLENES - PREPARATION OF FUNCTIONALIZED 1,2,4-TRISUBSTITUTED-1,3-DIENES [J].
ARCADI, A ;
BERNOCCHI, E ;
BURINI, A ;
CACCHI, S ;
MARINELLI, F ;
PIETRONI, B .
TETRAHEDRON LETTERS, 1989, 30 (26) :3465-3468
[10]   THE PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS - A ROUTE TO GAMMA,GAMMA-DIARYL ALLYLIC ALCOHOLS [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F .
TETRAHEDRON, 1985, 41 (22) :5121-5131