Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system

被引:77
作者
Pehlivan, Leyla [1 ]
Metay, Estelle [1 ]
Laval, Stephane [1 ]
Dayoub, Wissam [1 ]
Demonchaux, Patrice [2 ]
Mignani, Gerard [3 ]
Lemaire, Marc [1 ]
机构
[1] Univ Lyon 1, CNRS, ICBMS, Lab Catalyse & Synthese Organ,UMR5246, F-69622 Villeurbanne, France
[2] Minakem SAS, F-59310 Beuvry La Foret, France
[3] Lyon Res Ctr, F-69192 St Fons, France
关键词
SELECTIVE REDUCTION; CHEMOSELECTIVE HYDROGENATION; HYDROSILYLATION; PLATINUM; NITROCOMPOUNDS; NITROARENES;
D O I
10.1016/j.tet.2010.12.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac)(3) is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1971 / 1976
页数:6
相关论文
共 39 条
  • [1] Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones
    Addis, Daniele
    Shaikh, Nadim
    Zhou, Shaolin
    Das, Shoubhik
    Junge, Kathrin
    Beller, Matthius
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1687 - 1691
  • [2] Bechamp A., 1854, Anal. Chim. Phys, V42, P186
  • [3] AN AIR-STABLE CATALYST SYSTEM FOR THE CONVERSION OF ESTERS TO ALCOHOLS (VOL 57, PG 3751, 1992)
    BERK, SC
    BUCHWALD, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) : 3221 - 3221
  • [4] The reduction of nitrobenzenes by triethylsilane using Wilkinson's catalyst
    Brinkman, HR
    Miles, WH
    Hilborn, MD
    Smith, MC
    [J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (05) : 973 - 980
  • [5] On the Role of Metal Contaminants in Catalyses with FeCl3
    Buchwald, Stephen L.
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5586 - 5587
  • [6] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
    CHUIT, C
    CORRIU, RJP
    REYE, C
    YOUNG, JC
    [J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1371 - 1448
  • [7] Transforming nonselective into chemoselective metal catalysts for the hydrogenation of substituted nitroaromatics
    Corma, Avelino
    Serna, Pedro
    Concepcion, Patricia
    Juan Calvino, Jose
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8748 - 8753
  • [8] Chemoselective hydrogenation of nitro compounds with supported gold catalysts
    Corma, Avelino
    Serna, Pedro
    [J]. SCIENCE, 2006, 313 (5785) : 332 - 334
  • [9] ON THE SYNTHESIS OF SULFONATED DERIVATIVES OF 4-AMINOINDAN AND 5-AMINOINDAN
    COURTIN, A
    [J]. HELVETICA CHIMICA ACTA, 1980, 63 (08) : 2280 - 2286
  • [10] Highly Chemo- and Regioselective Reduction of Aromatic Nitro Compounds Using the System Silane/Oxo-Rhenium Complexes
    de Noronha, Rita G.
    Romao, Carlos C.
    Fernandes, Ana C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) : 6960 - 6964