Suzuki-Miyaura cross-coupling of arenediazonium salts with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium catalyst

被引:43
作者
Qin, Yuancheng [1 ]
Wei, Wei [1 ]
Luo, Meiming [1 ]
机构
[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
关键词
Suzuki reaction; arenediazonium salts; N-heterocyclic; carbene-palladium complex; polymer-supported catalyst; recyclable catalyst;
D O I
10.1055/s-2007-986627
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Suzuki-Miyaura cross-coupling of arenediazonium salts with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-Pd complex catalyst has been achieved for the first time. The reaction was performed at room temperature under aerobic conditions to give biaryls in good to excellent yields in the absence of a base. The supported catalyst could be reused several times and still retained its high activity.
引用
收藏
页码:2410 / 2414
页数:5
相关论文
共 42 条
[1]   Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling [J].
Andrus, MB ;
Song, C .
ORGANIC LETTERS, 2001, 3 (23) :3761-3764
[2]   Reactions of dry arenediazionium o-benzenedisulfonimides with triorganoindium compounds [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Giaveno, Cinzia .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) :4884-4890
[3]   Preparation of polymer-supported palladium/N-heterocyclic carbene complex for Suzuki cross-coupling reactions [J].
Byun, JW ;
Lee, YS .
TETRAHEDRON LETTERS, 2004, 45 (09) :1837-1840
[4]   Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts [J].
Cella, R ;
Cunha, RLOR ;
Reis, AES ;
Pimenta, DC ;
Klitzke, CF ;
Stefani, HA .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :244-250
[5]   Synthesis of a novel C2-symmetric thiourea and its application in the Pd-catalyzed cross-coupling reactions with arenediazonium salts under aerobic conditions [J].
Dai, MJ ;
Liang, B ;
Wang, CH ;
Chen, JH ;
Yang, Z .
ORGANIC LETTERS, 2004, 6 (02) :221-224
[6]   Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium [J].
Darses, S ;
Genet, JP ;
Brayer, JL ;
Demoute, JP .
TETRAHEDRON LETTERS, 1997, 38 (25) :4393-4396
[7]   Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium [J].
Darses, S ;
Jeffery, T ;
Genet, JP ;
Brayer, JL ;
Demoute, JP .
TETRAHEDRON LETTERS, 1996, 37 (22) :3857-3860
[8]  
Darses S, 1999, EUR J ORG CHEM, V1999, P1875
[9]   Cross-coupling reactions of arylsilanols with substituted aryl halides [J].
Denmark, SE ;
Ober, MH .
ORGANIC LETTERS, 2003, 5 (08) :1357-1360
[10]   Ionic liquids as reaction media for palladium-catalysed cross-coupling of aryldiazonium tetrafluoroborates with potassium organotrifluoroborates [J].
Gallo, V ;
Mastrorilli, P ;
Nobile, CF ;
Paolillo, R ;
Taccardi, N .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (03) :582-588