Transition-Metal-Free Oxidative Homocoupling of Aryl, Alkenyl, and Alkynyl Grignard Reagents with TEMPO

被引:39
作者
Maji, Modhu Sudan [1 ]
Studer, Armido [1 ]
机构
[1] Univ Munster, NRW Grad Sch Chem, Inst Organ Chem, D-48149 Munster, Germany
来源
SYNTHESIS-STUTTGART | 2009年 / 14期
关键词
Grignard reagents; oxidative homocoupling; alkoxyamine; nitroxide; persistent radicals; COUPLING REACTIONS; ARYLBORONIC ACIDS;
D O I
10.1055/s-0029-1216859
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative homocoupling of aryl, alkenyl, and alkynyl Grignard reagents by using commercially available TEMPO as an organic oxidant is described. These coupling reactions occur highly efficiently without the presence of any transition metal.
引用
收藏
页码:2467 / 2470
页数:4
相关论文
共 32 条
[1]   C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158
[2]   Rapid and easy access to (E)-1,3-enynes, 1,3-diynes and allenes starting from propargylic acetals, exploiting the different reactivity of lithium and mixed lithium-potassium organometallic reagents [J].
Blangetti, Marco ;
Deagostino, Annamaria ;
Rosso, Helena ;
Prandi, Cristina ;
Zavattaro, Chiara ;
Venturello, Paolo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (35) :5867-5874
[3]   Stereoselective radical-radical coupling reactions of metallated imidazolines [J].
Dalko, PI .
TETRAHEDRON LETTERS, 1999, 40 (21) :4035-4036
[4]  
Guin J., 2008, ANGEW CHEM, V120, P8855
[5]   Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO [J].
Guin, Joyram ;
De Sarkar, Suman ;
Grimme, Stefan ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8727-8730
[6]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[7]   Directed Palladium-Catalyzed Oxidative C-H Arylation of (Hetero)arenes with Arylboronic Acids by Using TEMPO [J].
Kirchberg, Sylvia ;
Vogler, Thomas ;
Studer, Armido .
SYNLETT, 2008, (18) :2841-2845
[8]  
Knochel, 2003, ANGEW CHEM, V115, P4438, DOI DOI 10.1002/ANGE.200300579
[9]   Highly functionalized organomagnesium reagents prepared through halogen-metal exchange [J].
Knochel, P ;
Dohle, W ;
Gommermann, N ;
Kneisel, FF ;
Kopp, F ;
Korn, T ;
Sapountzis, I ;
Vu, VA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4302-4320
[10]  
Krasovskiy A., 2006, ANGEW CHEM, V118, P5132