Magnetically separable Fe3O4 nanoparticles: an efficient catalyst for the synthesis of propargylamines

被引:138
作者
Sreedhar, B. [1 ]
Kumar, A. Suresh [1 ]
Reddy, P. Surendra [1 ]
机构
[1] Indian Inst Chem Technol, Council Sci & Ind Res, Inorgan & Phys Chem Div, Hyderabad 500607, Andhra Pradesh, India
关键词
Propargylamines; Magnetically separable Fe3O4 nanoparticles; Terminal alkynes; Amines; Aldehydes; 3-COMPONENT COUPLING REACTION; TERMINAL ALKYNES; DIRECT-ADDITION; ALDEHYDE; COPPER; AMINE; COMPLEX; SILVER; HYDROGENATION; CONDENSATION;
D O I
10.1016/j.tetlet.2010.02.016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Magnetically separable Fe3O4 nanoparticles endow with all efficient and economic route for the synthesis of propargylamines by the three-component Coupling of aldehyde, amine, and alkyne through C-H activation. The reaction is especially effective for reactions involving aliphatic aldehydes and no additional co-catalyst or activator is required. High catalytic activity and ease of recovery using all external magnetic field are additional eco-friendly attributes of this catalytic system. The catalyst was recycled for five times without a significant loss of catalytic activity. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1891 / 1895
页数:5
相关论文
共 58 条
[1]   Homoleptic trimethylsilylacetylide complexes of chromium(III), iron(II), and cobalt(III): Syntheses, structures, and ligand field parameters [J].
Berben, LA ;
Long, JR .
INORGANIC CHEMISTRY, 2005, 44 (23) :8459-8468
[2]   Enantioselective one-pot three-component synthesis of propargylamines [J].
Bisai, Alakesh ;
Singh, Vinod K. .
ORGANIC LETTERS, 2006, 8 (11) :2405-2408
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]  
Boulton AA, 1997, DRUG DEVELOP RES, V42, P150, DOI 10.1002/(SICI)1098-2299(199711/12)42:3/4<150::AID-DDR6>3.0.CO
[5]  
2-P
[6]   Iron-catalyzed three-component coupling of aldehyde, alkyne, and amine under neat conditions in air [J].
Chen, Wen-Wen ;
Nguyen, Rene V. ;
Li, Chao-Jun .
TETRAHEDRON LETTERS, 2009, 50 (24) :2895-2898
[7]   Hydroxyapatite supported copper catalyst for effective three-component coupling [J].
Choudary, BM ;
Sridhar, C ;
Kantam, ML ;
Sreedhar, B .
TETRAHEDRON LETTERS, 2004, 45 (39) :7319-7321
[8]   Asymmetric multicomponent copper catalyzed synthesis of chiral propargylamines [J].
Colombo, Federica ;
Benaglia, Maurizio ;
Orlandi, Simonetta ;
Usuelli, Fabio .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 260 (1-2) :128-134
[9]   Trends in back-bonding in the series trans-[M(C=CR)Cl(PH3)4] (M = Fe, Ru, Os; R = H, Ph, C6H4NO2-4) [J].
Delfs, CD ;
Stranger, R ;
Humphrey, MG ;
McDonagh, AM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) :208-212
[10]   Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex [J].
Fischer, C ;
Carreira, EM .
ORGANIC LETTERS, 2001, 3 (26) :4319-4321