Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions

被引:60
作者
Sharghi, Hashem [1 ]
Ebrahimpourmoghaddam, Sakineh [1 ]
Doroodmand, Mohammad Mahdi [1 ]
机构
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran
关键词
alpha-Aminophosphonates; Carbon nanotubes; Heterogeneous catalyst; Iron-doped; Organophosphorus; beta-Phosphonomalonates; Solvent free; ONE-POT SYNTHESIS; FREE KNOEVENAGEL CONDENSATIONS; ALPHA-AMINO PHOSPHONATES; MICHAEL ADDITION; FACILE SYNTHESIS; AMINOPHOSPHONATES; ALDEHYDES; PHOSPHITES; WATER; NANOPARTICLES;
D O I
10.1016/j.tet.2013.03.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated alpha-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines and carbonyl compounds. It also enabled the development of one-pot synthesis of beta-phosphonomalonates during the reaction of carbonyl compounds, malononitrile and phosphorus compounds. Excellent results were obtained in each case affording the corresponding organophosphorus adducts in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4708 / 4724
页数:17
相关论文
共 76 条
[1]   Nano ceria catalyzed synthesis of α-aminophosphonates under ultrasonication [J].
Agawane, Sandeep M. ;
Nagarkar, Jayashree M. .
TETRAHEDRON LETTERS, 2011, 52 (27) :3499-3504
[2]   FIRE-RETARDANT POLYMERS - POLYMERIZATION OF 1-OXO-2,6,7-TRIOXA-1-PHOSPHABCYCLO[2,2,2]OCT-4-YLMETHYL METHACRYLATE, AND ITS COPOLYMERIZATION WITH METHYL-METHACRYLATE, STYRENE, AND TRIALLYLCYANURATE [J].
ALLEN, DW ;
ANDERTON, EC ;
BRADLEY, C ;
SHIEL, LE .
POLYMER DEGRADATION AND STABILITY, 1995, 47 (01) :67-72
[3]   An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate [J].
Bhagat, Srikant ;
Chakraborti, Asit K. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1263-1270
[4]  
BODALSKI R, 1972, TETRAHEDRON LETT, P4209
[5]  
Castell E., 1998, [No title captured], Patent No. [9807698, WO 9807698]
[6]   Catalytic properties of several palladium complexes covalently anchored onto silica for the aerobic oxidation of alcohols [J].
Choudhary, D ;
Paul, S ;
Rajive, GA ;
Clark, JH .
GREEN CHEMISTRY, 2006, 8 (05) :479-482
[7]   Organic Reactions in Water: A Distinct Novel Approach for an Efficient Synthesis of α-Amino Phosphonates Starting Directly from Nitro Compounds [J].
Das, Biswanath ;
Satyalakshmi, Gandham ;
Suneel, Kanaparthy ;
Damodar, Kongara .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8400-8402
[8]   Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group [J].
Demmer, Charles S. ;
Krogsgaard-Larsen, Niels ;
Bunch, Lennart .
CHEMICAL REVIEWS, 2011, 111 (12) :7981-8006
[9]   The phospha-Michael addition in organic synthesis [J].
Enders, D ;
Saint-Dizier, A ;
Lannou, MI ;
Lenzen, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :29-49
[10]   ENANTIOSELECTIVE HANTZSCH DIHYDROPYRIDINE SYNTHESIS VIA METALATED CHIRAL ALKYL ACETOACETATE HYDRAZONES [J].
ENDERS, D ;
MULLER, S ;
DEMIR, AS .
TETRAHEDRON LETTERS, 1988, 29 (49) :6437-6440