Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles

被引:317
作者
Taillefer, Marc [1 ]
Xia, Ning [1 ]
Ouali, Armelle [1 ]
机构
[1] Ecole Natl Super Chim Montpellier, CNRS, UMR 5076, F-34296 Montpellier 5, France
关键词
copper; cross-coupling; iron; nitrogen heterocycles;
D O I
10.1002/anie.200603173
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) An ideal pair: Various substituted aryl halides react under mild conditions with nitrogen heterocycles in the presence of catalytic amounts of [Fe(acac)3] (acac = acetylacetonate) and copper salts to give the corresponding cross-coupling products in high yields (see scheme). This cheap and environmentally friendly cocatalyst system is the first example of cooperative Fe/Cu catalysis in this type of N-C bond formation. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:934 / 936
页数:3
相关论文
共 38 条
[1]   Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Goodby, JW ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2004, (24) :2822-2823
[2]   Pd- and Cu-catalyzed selective arylation of benzotriazole [J].
Beletskaya, IP ;
Davydov, DV ;
Moreno-Mañas, M .
TETRAHEDRON LETTERS, 1998, 39 (31) :5617-5620
[3]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[4]  
Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199
[5]   Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides [J].
Cristau, HJ ;
Ouali, A ;
Spindler, JF ;
Taillefer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2483-2492
[6]   Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622
[7]   A general and mild Ullmann-type synthesis of diaryl ethers [J].
Cristau, HJ ;
Cellier, PP ;
Hamada, S ;
Spindler, JF ;
Taillefer, M .
ORGANIC LETTERS, 2004, 6 (06) :913-916
[8]   Mild conditions for copper-catalysed N-arylation of pyrazoles [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709
[9]  
Dohle W, 2001, SYNLETT, P1901
[10]   Unusual structure and reactivity of a homoleptic "super-ate" complex of iron:: Implications for Grignard additions, cross-coupling reactions, and the Kharasch deconjugation [J].
Fürstner, A ;
Krause, H ;
Lehmann, CW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (03) :440-444