A New Strategy for the Aminolysis of Epoxides with Amines Under Solventfree Conditions Using Fe-Mcm-41 as a Novel and Ef
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A New Strategy for the Aminolysis of Epoxides with Amines Under Solventfree Conditions Using Fe-Mcm-41 as a Novel and Efficient Catalyst Majid M. Heravi Æ Bita Baghernejad Æ Hossein A. Oskooie
Received: 7 January 2009 / Accepted: 4 February 2009 / Published online: 24 February 2009 Ó Springer Science+Business Media, LLC 2009
Abstract A highly efficient method for the aminolysis of epoxides in the presence of a catalytic amount of Fe-MCM41 is reported. An important advantage of this catalyst is the ease of separating it from the reaction mixture, as well as the fact that it could be recycled a number of times. Keywords Reused
Fe-MCM-41 Aminolysis Epoxides
1 Introduction Epoxides are well known carbon electrophiles capable of reacting with various nucleophiles and their ability to undergo regioselective ring opening reactions contributes to their synthetic value. They are one of the most important synthetic intermediates in organic synthesis and a variety of reagents are known to nucleophilically open the ring. They can also serve as good chiral ligands of some asymmetric metal complex catalysts [1]. Among them, reaction of epoxide with amines is particularly interesting, because it leads to the formation of
M. M. Heravi (&) B. Baghernejad H. A. Oskooie Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran e-mail: [email protected] B. Baghernejad e-mail: [email protected] M. M. Heravi Depatrment of Chemistry, School of Sciences, Islamic Azad University, Mashhad-Branch, Mashhad, Iran
b-aminoalcohols which are intermediates in the synthesis of biologically active natural and synthetic products, pharmaceuticals synthetic amino acids and pesticides [2–5]. They are also used as blockers, insecticidal agents and as chiral ligands in asymmetric synthesis [2]. Several methods have been reported in the literature for the synthesis of b-aminoalcohols and several catalysts including sulfamic acid [6] Amberlyst-15 [7] metal triflates [8] metal alkoxides [9] metal halides [10, 11] transition metal salts [12, 13] heteropolymolybdate or tungstate [14] monodispersed silica nanoparticles [15] zeolites [16] montmorillonite clay [17], and ionic liquids [18] have been reported for this synthesis. However, the use of hazardous organic solvents, low catalytic efficiency and product selectivity, and non-reusability of the catalyst system are some of the issues with the existing methods. Less basic amines fail to open the epoxide ring at ambient conditions and require higher temperatures. In most cases, the reactions were carried out with aromatic amines only. Hence, there is a need for a more active and selective heterogeneous catalyst for this reaction. The possibility of performing multi-component reactions under solvent-free conditions with solid catalysts could enhance their efficiency from an economic as well as an ecological point of view, so solvent free chemical reactions have received much attention. These reactions offer several advantages in preparative procedures such as envi
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