Greener and regioselective ring opening of epoxides with TMSCN using potassium salts of magnetic carbon nitride
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RIGINAL PAPER
Greener and regioselective ring opening of epoxides with TMSCN using potassium salts of magnetic carbon nitride Mostafa Saadat1 · Mahnaz Qomi1 · Najmedin Azizi2 Received: 9 May 2020 / Accepted: 14 September 2020 / Published online: 14 October 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract Potassium salts of magnetic graphitic carbon nitride ( Fe3O4@g-C3N4-K) synthesized and proved to be a green and recyclable catalyst for rapid and regioselective ring opening of epoxides with TMSCN, yielding the β-hydroxynitrile ring-opened products under mild reaction conditions. It is manageable to large-scale preparation with simple instruments and gives the desired compounds in short reaction times with good-to-excellent yields (73–95%) under solvent-free conditions. Magnetic separation protocol has used to achieve a simple separation and reuse of catalysts from unpurified reaction mixtures using external magnets without loss of catalytic operation after five cycles. Graphic abstract
Keywords Ionic catalyst · Graphitic carbon nitride · TMSCN · Ring opening of epoxides · Hydroxy nitrile
Introduction Green Chemistry, the design of chemical processes to minimize the environmental pollution caused by solvents in industry and retail, is a comprehensive strategy [1, 2]. Solvent-free synthesis is receiving significant as a tool for the combination of a broad range of useful and essential biologically active compounds to improve old methodologies making them more clean, safe, and comfortable to perform [3–5]. Furthermore, solvent-free reactions can moreover be enhanced to take advantage of utilizing nonconventional * Najmedin Azizi [email protected] 1
Active Pharmaceutical Ingredients Research Center (APIRC), Tehran Medical Sciences, Islamic Azad University, Tehran, Iran
Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335‑186, Tehran, Iran
2
energy sources, such as microwaves, ultrasound, and ball milling alternative to conventional heating to increase the efficiency of the reactions [6]. Carbon-based composites are smart support material for potential applications in the field of gas adsorption, heterogeneous catalysis, water treatment, energy storage, and conversion devices [7, 8]. Among the carbon composite, carbon nitrides (CNs) are fascinating materials with distinctive properties due to their high chemical and mechanical stability, availability, and ease of functionalization [9–11]. The features of the CN materials mostly controlled by the structure, nitrogen contents, source of starting material, temperature, and carbon precursors [12–14]. In this context, it is possible to optimize their properties such as surface areas and tunable pore diameters for specific applications. Furthermore, CN materials can straightforwardly produce from cheap nitrogen-rich organic molecules such as melamine or urea derivatives under thermal treatment [15–18].
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