Cu(I)@Isatin-Glycine-Boehmite nanoparticles: as novel heterogeneous catalyst for the synthesis and selective oxidation o
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ORIGINAL PAPER
Cu(I)@Isatin‑Glycine‑Boehmite nanoparticles: as novel heterogeneous catalyst for the synthesis and selective oxidation of sulfides Arash Ghorbani‑Choghamarani1,2 · Rokhsareh Sahraei1 · Zahra Taherinia1 · Masoud Mohammadi1 Received: 25 April 2020 / Accepted: 21 September 2020 © Iranian Chemical Society 2020
Abstract This work present the synthesis of Cu (I) immobilized on modified boehmite nanoparticles as an environmentally friendly heterogeneous catalyst for the synthesis of sulfides and their oxidation to the corresponding sulfoxides in good to excellent yields. The structure of the catalyst was studied by scanning electron microscopy, X-ray diffraction, thermogravimetric, inductively coupled plasma atomic emission spectroscopy, and Brunauer–Emmett–Teller techniques. The use of this heterogeneous nanocatalyst in mentioned organic reactions allowed achieving good results such as the excellent stability, high efficiency, low cost, easy recovery, and reusability of catalyst for four continuous cycles. Graphic abstract
Keywords Boehmite nanoparticles · Copper · Thiourea · Sulfide · Sulfoxide
Introduction
* Arash Ghorbani‑Choghamarani [email protected]; [email protected] 1
Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran
Department of Organic Chemistry, Bu-Ali Sina University, 6517838683 Hamedan, Iran
2
Organosulfur materials have become increasingly useful and important in organic synthesis, which have been widely used in biological [1], pharmaceutical [2], and material chemistry [3]. The traditional method for the synthesis of aryl sulfides are based on condensation of arenethiols with aryl halides, [4] treatment of aryl lithium or Grignard reagents with sulfurated electrophiles [5] or reduction of sulfones to sulfoxides, which this conversion can be achieved
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selectively in the presence of strong reducing agents, such as DIBAL-H [6] or LiALH4.[7]. However, most of these methods suffer from considerable practical limitations in foul-smelling, volatile, and toxic, which can cause environmental and safety problems. More recently, sulfur transfer reagents were found to be suitable as alternative to thiols in the presence of palladium, [8] nickel, [9] copper, [10] Fe [11], and Zr [12] based catalytic systems for this purpose. Supported metallic nanoparticles and their catalytic applications due to their reactive morphologies have received significant attention in recent years [13]. In fact, nanoparticles have a strong tendency to agglomerate and oxidize due to high surface energy in aqueous solutions, it is important to find a method to solve this problem [14]. In many cases, metal nanoparticles are immobilized or synthesized on various supports, such as pyridiniumporphyrazinato [15], multiwall carbon nanotube [16], magnetic, [17–26] zeolites, [27] microspheres, [28] SBA-15, [29, 30] MCM-41, [31, 32] and boehmite [33, 34]. Among these supports, boehmite has several attractive features, such as: non-toxic prop
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