Iron- and Cobalt-Catalyzed Arylation of Azetidines, Pyrrolidines, and Piperidines with Grignard Reagents

被引:56
作者
Barre, Baptiste [1 ]
Gonnard, Laurine [1 ]
Campagne, Remy [1 ]
Reymond, Sebastien [1 ]
Marin, Julien [2 ]
Ciapetti, Paola [2 ]
Brellier, Marie [2 ]
Guerinot, Amandine [1 ]
Cossy, Janine [1 ]
机构
[1] PSL Res Univ, CNRS, UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI,ESPCI, F-75231 Paris 05, France
[2] NovAliX, F-67405 Illkirch Graffenstaden, France
关键词
SECONDARY ALKYL-HALIDES; CROSS-COUPLING REACTIONS; ARYL; BROMIDES;
D O I
10.1021/ol503043r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.
引用
收藏
页码:6160 / 6163
页数:4
相关论文
共 52 条
[1]  
Allerton C. M. N., 2006, PCT International Application, Patent No. [WO 2006134487, 2006134487]
[2]  
Allerton C. M. N., 2005, U.S. Patent Application, Patent No. 20050267096
[3]   Metal-Free Coupling of Saturated Heterocyclic Sulfonylhydrazones with Boronic Acids [J].
Allwood, Daniel M. ;
Blakemore, David C. ;
Brown, Alan D. ;
Ley, Steven V. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) :328-338
[4]  
[Anonymous], 2010, [No title captured], Patent No. [20100216764, US P. 20100216764]
[5]   Cobalt-catalyzed cross-coupling reaction of arylzinc reagents with ethyl bromodifluoroacetate [J].
Araki, Keisuke ;
Inoue, Munenori .
TETRAHEDRON, 2013, 69 (19) :3913-3918
[6]   An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides [J].
Bica, K ;
Gaertner, P .
ORGANIC LETTERS, 2006, 8 (04) :733-735
[7]  
Billotte S, 1998, SYNLETT, P379
[8]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[9]   Novel syntheses of azetidines and azetidinones [J].
Brandi, Alberto ;
Cicchi, Stefano ;
Cordero, Franca M. .
CHEMICAL REVIEWS, 2008, 108 (09) :3988-4035
[10]  
Buckingham J., 2009, DICT ALKALOIDS