Efficient copper-free PdCl2(PCy3)2-catalyzed Sonogashira coupling of aryl chlorides with terminal alkynes

被引:143
作者
Yi, CY [1 ]
Hua, RM [1 ]
机构
[1] Tsinghua Univ, Dept Chem, Innovat Catalysis Program, Key Lab Organ Optoelect & Mol Engn,Minist Educ, Beijing 100084, Peoples R China
关键词
D O I
10.1021/jo0525175
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Under copper-free conditions and with Cs2CO3 as a base, PdCl2(PCy3)(2) showed high catalytic activity for cross-coupling of electron-rich, electron-neutral, and electron-deficient aryl chlorides with a variety of terminal alkynes in DMSO at 100-120 degrees C affording internal arylated alkynes in good to excellent yields.
引用
收藏
页码:2535 / 2537
页数:3
相关论文
共 37 条
[1]   A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368
[2]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[3]   A copper- and amine-free Sonogashira coupling reaction promoted by a ferrocene-based phosphinimine-phosphine ligand at low catalyst loading [J].
Arques, A ;
Auñon, D ;
Molina, P .
TETRAHEDRON LETTERS, 2004, 45 (22) :4337-4340
[4]   Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water [J].
Bhattacharya, S ;
Sengupta, S .
TETRAHEDRON LETTERS, 2004, 45 (47) :8733-8736
[5]  
Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO
[6]  
2-X
[7]   A copper- and amine-free sonogashira reaction employing aminophosphines as ligands [J].
Cheng, J ;
Sun, YH ;
Wang, F ;
Guo, MJ ;
Xu, JH ;
Pan, Y ;
Zhang, ZG .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5428-5432
[8]   Nonpolar biphasic catalysis: Sonogashira and Suzuki coupling of aryl bromides and chlorides [J].
Datta, A ;
Plenio, H .
CHEMICAL COMMUNICATIONS, 2003, (13) :1504-1505
[9]   Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines [J].
DeVasher, RB ;
Moore, LR ;
Shaughnessy, KH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7919-7927
[10]   Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites [J].
Djakovitch, L ;
Rollet, P .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1782-1792