Iron-catalyzed alkylations of aromatic Grignard reagents

被引:275
作者
Cahiez, Gerard [1 ]
Habiak, Vanessa [1 ]
Duplais, Christophe [1 ]
Moyeux, Alban [1 ]
机构
[1] UCP, UMR 8123, CNRS, ESCOM,Lab Synth Organ Select & Chim Organomet, F-95092 Cergy Pontoise, France
关键词
cross-coupling; Grignard reagents; homogeneous catalysis; iron; sustainable chemistry;
D O I
10.1002/anie.200700742
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Any old iron: Two efficient iron-catalyzed cross-coupling reactions between aryl Grignard reagents and alkyl bromides were developed that are suitable for large-scale applications. The first procedure uses iron acetylacetonate and involves a cooperative effect between the two ligands N,N,N′,N′-tetramethylethylenediamine (TMEDA) and hexamethylenetetraamine (HMTA), while the second procedure uses [(FeCl 3)2(tmeda)3] as catalyst. 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4364 / 4366
页数:3
相关论文
共 29 条
[1]   A square-planar organoiron(III) compound with a spin-admixed state [J].
Alonso, Pablo J. ;
Arauzo, Ana B. ;
Fornies, Juan ;
Garcia-Monforte, M. Angeles ;
Martin, Antonio ;
Martinez, Jesus I. ;
Menjon, Babil ;
Rillo, Conrado ;
Saiz-Garitaonandia, Jose J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6707-6711
[2]  
[Anonymous], 2004, ANGEW CHEM
[3]  
[Anonymous], 2002, ANGEW CHEM
[4]  
[Anonymous], 2006, ANGEW CHEM INT EDIT
[5]   Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary 2 alkyl halides with aryl Grignard reagents [J].
Bedford, RB ;
Betham, M ;
Bruce, DW ;
Danopoulos, AA ;
Frost, RM ;
Hird, M .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) :1104-1110
[6]   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
[7]   Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163
[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]  
Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199
[10]   Highly chemo- and stereoselective Fe-catalyzed alkenylation of organomanganese reagents [J].
Cahiez, G ;
Marquais, S .
TETRAHEDRON LETTERS, 1996, 37 (11) :1773-1776