Short Communication Synthesis, characterization and application of magnetic room temperature dicationic ionic liquid as an efficient catalyst for the preparation of 1,2-azidoalcohols Bijan Mombani Godajdar a, ⁎, Ali Reza Kiasat b , Mohammad Mahmoodi Hashemi c a Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran b Department of Chemistry, College of Science, Shahid Chamran University, Ahwaz, Iran c Department of Chemistry, Sharif University of Technology, Tehran, Iran abstract article info Article history: Received 24 December 2012 Received in revised form 24 March 2013 Accepted 26 March 2013 Available online 18 April 2013 Keywords: Regioselective Magnetic room temperature dicationic ionic liquid 1,2-azidoalcohols Green chemistry An environmentally benign, aqueous synthesis of 1,2-azidoalcohols via regioselective ring opening of their epoxides using magnetic imidazolium based dicationic room temperature ionic liquid, [pbmim](FeCl 4 ) 2 , as an efficient magnetic phase transfer catalyst in water has been described. The present approach offers the ad- vantages of clean reaction, simple methodology, short reaction time, high yield, easy purification and reus- able catalyst. © 2013 Elsevier B.V. All rights reserved. 1. Introduction In recent years, the concept of green chemistry has been playing an important role for meeting the fundamental scientific challenges of protecting the living environment [1]. Green chemistry, also known as sustainable chemistry, is the design of chemical products and processes that reduce or eliminate the use or generation of haz- ardous substances. Again, organic synthesis in aqueous media is rap- idly gaining importance in view of the fact that the use of many toxic and volatile organic solvents, particularly chlorinated hydrocarbons, contributes to pollution [2]. Consequently, it is highly desirable to de- velop environmentally benign processes that can be conducted in aqueous media. Furthermore, using water as a solvent offers many advantages, such as simple operation, abundant in nature, has virtual- ly no cost, and the safest among all available solvents. However, its use is limited by the low solubility of organic compounds. One of the most important strategies to overcome this limitation is the utili- zation of phase transfer catalyst such as ionic liquid (IL). Room temperature ionic liquids (RTILs) are generally defined as salts that are liquid at or below room temperature. The combination of ammonium, pyridinium, phosphonium or imidazolium cations with various inorganic or organic anions led to a large amount of liquid salts with numerous possible applications e.g. in the field of organic synthesis, catalysis, biocatalysis, material science, chemical engineering, electrochemistry or separation processes [3]. The increasing interest in RTILs is related to their possible exploitation as environmentally friend- ly neoteric solvents because of their vanishing vapor pressure, thermal and chemical stability, air and moisture stability, wide liquidus range, solvent capability, etc. [4]. However the large scale application of ionic liquids is still far from realization because of their high cost and difficult recovery [5]. Magnetic ILs not only have the excellent properties of IL but also exhibit an unexpectedly strong response to an additional magnet. These properties make magnetic ILs have more advantages and po- tential application prospects than conventional ILs in the fields of cat- alytic reactions, solvent effects and separation processes [6]. Vicinal azidoalcohols are an important class of organic compounds and they serve as precursors in the synthesis of vicinal aminoalcohols, carbohydrates, nucleosides [7–9], lactames [10], and oxazolines [11]. They are usually prepared through ring opening of epoxides by using different kinds of azides in suitable solvents. The reactions often carried out under either alkaline or acidic conditions and sever- al different methods have been devised in order to obtain the direct azidolyses of epoxides in the presence of sodium azide [12]. Under these conditions, azidolyses are usually carried out over a long reac- tion times and azidohydrin is often accompanied by isomerization, epimerization, and rearrangement of products [13,14]. In order to overcome some of these limitations, a number of alternative proce- dures have been reported over the past few years using a variety of catalysts [15–18]. However, most of these methods have limitations including use of expensive catalyst or solvent, strong acidic condi- tions, low regioselectivity, longer reaction time, and harsh reaction conditions. Thus, the development of a new and efficient protocol Journal of Molecular Liquids 183 (2013) 14–19 ⁎ Corresponding author. Tel.: +98 916607003; fax: +98 611 3738044. E-mail address: bmombini@gmail.com (B.M. Godajdar). 0167-7322/$ – see front matter © 2013 Elsevier B.V. All rights reserved. http://dx.doi.org/10.1016/j.molliq.2013.03.022 Contents lists available at SciVerse ScienceDirect Journal of Molecular Liquids journal homepage: www.elsevier.com/locate/molliq