An efficient synthesis of propargylamines using a silica gel anchored copper chloride catalyst in an aqueous medium

被引:70
作者
Sreedhar, B. [1 ]
Reddy, P. Surendra [1 ]
Krishna, C. S. Vamsi [1 ]
Babu, P. Vijaya [1 ]
机构
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India
关键词
propargylamines; silica gel anchored copper chloride; mesoporous silica; terminal alkynes and imines;
D O I
10.1016/j.tetlet.2007.08.116
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design and development of a silica gel anchored copper chloride heterogeneous catalyst for the synthesis of propargylamines using an amine, an aldehyde, and an alkyne through C-H activation in water is described. Both aliphatic and aromatic aldehydes and amines are used for the reaction. The catalyst was recovered quantitatively by simple filtration and reused several times. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7882 / 7886
页数:5
相关论文
共 31 条
[1]   Recent advances in the synthesis, characterization and applications of mesoporous molecular sieves [J].
Beck, JS ;
Vartuli, JC .
CURRENT OPINION IN SOLID STATE & MATERIALS SCIENCE, 1996, 1 (01) :76-87
[2]   A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES [J].
BECK, JS ;
VARTULI, JC ;
ROTH, WJ ;
LEONOWICZ, ME ;
KRESGE, CT ;
SCHMITT, KD ;
CHU, CTW ;
OLSON, DH ;
SHEPPARD, EW ;
MCCULLEN, SB ;
HIGGINS, JB ;
SCHLENKER, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10834-10843
[3]  
BURKETT SL, 1996, CHEM COMMUN, P1961
[4]   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
[5]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[6]  
2-6
[7]   Functionalized monolayers on ordered mesoporous supports [J].
Feng, X ;
Fryxell, GE ;
Wang, LQ ;
Kim, AY ;
Liu, J ;
Kemner, KM .
SCIENCE, 1997, 276 (5314) :923-926
[8]   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
[9]   Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines [J].
Gommermann, N ;
Koradin, X ;
Polborn, K ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5763-5766
[10]  
Huma HZS, 2002, TETRAHEDRON LETT, V43, P6485