Homogeneous catalytic oxidation of alkenes employing mononuclear vanadium complex with hydrogen peroxide
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ORIGINAL PAPER
Homogeneous catalytic oxidation of alkenes employing mononuclear vanadium complex with hydrogen peroxide Abhishek Maurya1 Received: 24 April 2020 / Accepted: 26 June 2020 © Iranian Chemical Society 2020
Abstract Homogeneous liquid-phase oxidation of alkenes (allylbenzene, cis-cyclooctene, 4-chlorostyrene, styrene, 2-norbornene, 1-methyl cyclohexene, indene, lemonine, and 1-hexene) were catalyzed by using vanadium complex [VO(hyap)(acac)2] in existence of H2O2. The complex [VO(hyap)(acac)2] was formed as a crystal by the reaction of [VO(acac)2] and 2-hydroxyacetophenone (hyap) in the presence of methanol by refluxing the reaction mixture. Various analytical and spectroscopic techniques, namely FTIR, ESI–MS, UV–Vis, single-crystal XRD, and EPR, were used to analyze and optimize the structure of the complexes. Graphic abstract
Keywords Vanadium(IV) complex · Homogeneous catalysis · Alkenes oxidation
Introduction The most frequent catalytic oxidation is accommodated by transition metals that operate hydrogen peroxide (H2O2) or tert-butyl hydroperoxide (TBHP) for the Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-01988-x) contains supplementary material, which is available to authorized users. * Abhishek Maurya [email protected] 1
Department of Chemistry, Indian Institute of Technology (Indian School of Mines), Dhanbad, Jharkhand 826004, India
oxyfunctionalization of the organic substrates [1–3]. Generally, H2O2 and TBHP are the environmentally genial, clean, and comparatively low priced, commercially available and good looking oxidizing agent [1–5]. The oxidation reaction performed by metal catalysts depends on the metal center as well as the nature of the ligands [6–9]. Nitrogen or oxygencarrying ligands of vanadium complexes have been widely used as representative compounds for imitating the catalytic properties of mono-oxygenases [9, 10]. Vanadium ion attributes different oxidation states, such as oxovanadium (IV) and (V) [11, 12], with the common coordination numbers of 6 (octahedral), 5 (square pyramidal or trigonal bipyramidal), and 4 (tetrahedral) [13–15]. Vanadium can perform liquidphase oxidation reactions of alkanes, alcohols, alkenes,
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halides, aromatics through the heterogeneous or homogenous procedure [9, 14–26]. Thus, homogeneous liquid-phase oxidation reaction of C–H, C–C, and C=C bonds by applying vanadium complexes in the presence of peroxide is of basic significance in numerous field such as organic synthesis, pharmaceutical, laboratory, and industry [9, 16, 17, 20, 27, 28]. The fabrication of oxygen-containing products forming, oxidation of alkenes is very demanding for the industrial point as well as in practical organic synthesis. Epoxidation and oxidative cleavage are the key operations involved in the oxidation of alkenes [29–32]. The epoxidation products are very essential for industrial and synthetic purpose because most of the epoxide products are used in the synthesi
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