- Trace Detection of Hydrogen Peroxide via Dynamic Double Emulsions
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Hydrogen peroxide is a dynamic signaling molecule in biological systems. We report herein a versatile double emulsion sensor that can detect femtomolar quantities of aqueous hydrogen peroxide. The mechanism responsible for this sensitivity is a peroxide induced change in double emulsion structure, which results in a modified directional emission from dyes dissolved in the high index organic phase. The morphology (structure) of the double emulsion is controlled via interfacial tensions and a methyltrioxorhenium catalyzed sulfide oxidation results in an enhancement of the surfactant effectiveness. The incipient polar sulfoxide induced decrease of the interfacial tension at the organic-water (O-W) interface results in an increased interfacial area between the organic phase and water and a diminished emission perpendicular to the supporting substrate. The modularity of our sensory system is demonstrated through cascade catalysis between methyltrioxorhenium and oxidase enzymes, with the latter producing hydrogen peroxide as a byproduct to enable for the selective and sensitive detection of molecular and ionic enzymatic substrates.
- Fong, Darryl,Swager, Timothy M.
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- Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions
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Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]
- Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh
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p. 2420 - 2435
(2021/01/04)
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- Preparation of Ni-microsphere and Cu-MOF using aspartic acid as coordinating ligand and study of their catalytic properties in Stille and sulfoxidation reactions
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In this study, the thermal and catalytic behavior of Ni-microsphere and Cu-MOF were investigated with aspartic acid as the coordinating ligand with different morphologies. The Ni-microsphere and Cu-MOF with aspartic acid, as the coordinating ligand, were prepared via a solvothermal method. The morphology and porosity of the obtained Ni microsphere and Cu-MOF were characterized by XRD, FTIR, TGA, DSC, BET and SEM techniques. The catalytic activity of the Ni-microsphere and Cu-MOF was examined in Stille and sulfoxidation reactions. The Ni microsphere and Cu-MOF were easily isolated from the reaction mixtures by simple filtration and then recycled four times without any reduction of catalytic efficiency.
- Ghorbani-Choghamarani, Arash,Bastan, Hosna,Kakakhani, Zahra,Taherinia, Zahra
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p. 14905 - 14914
(2021/05/19)
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- Trisaminomethane–cobalt complex supported on Fe3O4 magnetic nanoparticles as an efficient recoverable nanocatalyst for oxidation of sulfides and C–S coupling reactions
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In this work, trisaminomethane–cobalt complex immobilized onto the surface of Fe3O4 magnetic nanoparticles was successfully prepared via a simple and inexpensive procedure. The prepared nanocatalyst was considered a robust and clean nanoreactor catalyst for the oxidation and synthesis of sulfides under green conditions. This ecofriendly heterogeneous catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffractometry, energy-dispersive X-ray spectroscopy, inductively coupled plasma-atomic emission spectroscopy, thermogravimetric analysis, vibrating sample magnetometry, X-ray mapping, scanning electron microscopy, and transmission electron microscopy techniques. Use of green medium, easy separation and workup, excellent reusability of the nanocatalyst, and short reaction time are some outstanding advantages of this method.
- Ashraf, Muhammad Aqeel,Liu, Zhenling,Peng, Wan-Xi
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- Fe3O4@MCM-41@Zn-Arg: as a novel, magnetically recoverable and ecofriendly nanocatalyst for the synthesis of disulfides, sulfoxides and 2,3-dihydroquinazolin?4(1H)?ones
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The direct supporting of Zn-arginine complex on magnetic core-shell nanostructures (Fe3O4@MCM-41@Zn-Arg) was reported as a novel, heterogeneous and excellent nanocatalyst, which applied for the oxidation reaction of sulfides to sulfoxides, oxidative coupling of thiols to their corresponding disulfides and the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under mild conditions. The structure of the catalyst was studied by X-Ray diffraction, Fourier transform-infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, atomic absorption spectroscopy, and vibrating sample magnetometry techniques. The simple experimental procedure, very good catalytic activity, low cost, and excellent recycling are the noteworthy features of the currently employed heterogeneous catalytic system.
- Nikoorazm, Mohsen,Erfani, Zahra
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p. 642 - 655
(2020/08/19)
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- Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst
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Nickel-anchored curcumin-functionalized boehmite nanoparticles (BNPs@Cur-Ni) as a robust and versatile nanocatalyst was synthesized and well-characterized by using Fourier transform infrared (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), X-ray mapping, thermogravimetric analysis (TGA), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), X-ray diffraction (XRD), and inductively coupled plasma optical emission spectroscopy (ICP-OES). The synthesis of 5-substituted 1H-tetrazoles and the oxidation of sulfides were conducted by BNPs@Cur-Ni with excellent turnover number (TON) and turnover frequency (TOF) outcomes. Also, the catalyst was reused for several sequential runs without Ni leaching or decreasing in reaction yield. Utilizing the curcumin and boehmite with a natural source as well as poly(ethylene glycol) (PEG) as a solvent in this simple protocol can be based on green chemistry rules.
- Jani, Muhammed Ali,Bahrami, Kiumars
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- Covalent immobilization of Co complex on the surface of SBA-15: Green, novel and efficient catalyst for the oxidation of sulfides and synthesis of polyhydroquinoline derivatives in green condition
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In this work, a green and novel catalyst was prepared through immobilization of cobalt complex on the surface of mesostructured SBA-15 and characterized by TGA, SEM, FT‐IR, EDX, ICP, BET and X-ray mapping analytical methods. This mesostructural material was used as an efficient and green interphase catalyst for the oxidation reactions and synthesis of polyhydroquinoline derivatives. All reactions were performed in short times and good yields. Moreover, the prepared catalyst could be used up to six runs without significant degradation in its catalytic activity or cobalt leaching.
- Ghorbani-Choghamarani, Arash,Mohammadi, Masoud,Tamoradi, Taiebeh,Ghadermazi, Mohammad
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- Immobilization of Pd(0) complex on the surface of SBA-15: A reusable catalyst for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides
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A simple and efficient method for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides in the presence of Pd(0) complex immobilized on mesoporous SBA-15 as an efficient, recoverable and thermally stable mesostructure has been reported. Also, the prepared mesostructure was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray mapping, energy-dispersive X-ray spectroscopy, N2 adsorption and desorption, inductively coupled plasma optical emission spectroscopy and thermal gravimetric analysis. Then, this mesostructured catalyst was applied in the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides. The approach described here offers advantages such as short reaction times, high yield, purity yields, simple and eco- friendly, easy work-up. More importantly, this nanohybrid robust catalyst did not undergo metal leaching and applied several times without any decrease in catalytic activity.
- Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
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p. 374 - 380
(2018/11/01)
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- Synthesis of new zirconium complex supported on MCM-41 and its application as an efficient catalyst for synthesis of sulfides and the oxidation of sulfur containing compounds
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In the present work, we report synthesis of new zirconium complex supported on mesoporous silica by anchoring of adenine on the wall of functionalized MCM-41, then reacted with ZrOCl2. The resultant MCM-41-Adenine-Zr was characterized by FT-IR, XRD, TEM, SEM, TGA, EDX, ICP and BET techniques. It was exhibited that the MCM-41-Adenine-Zr can be used as an efficient and thermally stable nanocatalyst for the oxidation of sulfides, oxidative coupling of thiols and synthesis of sulfides. Moreover, this heterogeneous catalyst can be easily recovered from the reaction mixture by simple filtration and reused for several consecutive cycles without noticeable change in its catalytic activity.
- Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
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- Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-one, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41
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Abstract: A simple, efficient and less expensive protocol for the synthesis of Cu(II) immobilized on MCM-41@Serine has been reported. This nanohybrid material was carefully characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, TEM, thermal gravimetric analysis, and N2 adsorption and desorption. The obtained nanostructured compound were also employed as a green, efficient, heterogeneous and reusable catalytic system for the synthesis of polyhydroquinoline, 2,3-dihydroquinazolin-4(1H)-one, sulfide and sulfoxide derivatives. High surface area, convenient recovery and reusability for several times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable reagents, good reaction times, simple practical methodology and ease of use all make Cu(II) immobilized on MCM-41@Serine a promising candidate for potential applications in some organic reactions; makes this protocol both attractive and economically viable. Graphical Abstract: MCM-41 nanostructured was prepared via simple and versatile procedure and directly immobilized with a new type of Cu–serine complex. After characterization of this catalyst, the catalytic activity of this nanostructure compound has been investigated for the synthesis of polyhydroquinoline, 2,3-dihydroquinazolin-4(1H)-one, sulfide and sulfoxide derivatives. [Figure not available: see fulltext.].
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 857 - 872
(2018/03/01)
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- Synthesis and characterization of oxo-vanadium complex anchored onto SBA-15 as a green, novel and reusable nanocatalyst for the oxidation of sulfides and oxidative coupling of thiols
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Abstract: The present work describes the synthesis of a new oxo-vanadium complex immobilized on SBA-15 nanostructure as an efficient catalyst for oxidation of sulfides and oxidative coupling of thiols. Characterization of the resultant AMPD@SBA-15 nanostructure was performed by various physico-chemical techniques such as Fourier transform infrared spectroscopy, transmission and scanning electron microscopies, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, thermal gravimetric analysis, and N2 adsorption and desorption. The results of the developed procedure bring several benefits such as the use of commercially available, ecologically benign, operational simplicity, and cheap and chemically inert reagents. It shows good reaction times, practicability and high efficiency, and is easily recovered from the reaction mixture by simple filtration and reused for several consecutive cycles without noticeable change in its catalytic activity. More importantly, high efficiency, simple and an inexpensive procedure, commercially available materials, easy separation, and an eco-friendly procedure are the several advantages of the currently employed heterogeneous catalytic system.
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash,Molaei, Somayeh
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p. 4259 - 4276
(2018/03/21)
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- Ni(II)-Adenine complex coated Fe3O4 nanoparticles as high reusable nanocatalyst for the synthesis of polyhydroquinoline derivatives and oxidation reactions
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In the present study, Fe3O4 nanoparticles were prepared via simple and versatile procedure. Then, a novel and green catalyst was synthesized by the immobilization of Ni on Fe3O4 nanoparticles coated with adenine. The activity of this nanostructure compound was examined for the oxidation of sulfides, oxidative coupling of thiols and synthesis of polyhydroquinolines. The prepared catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), inductively coupled plasma optical emission spectroscopy (ICP-OES), X-ray Diffraction (XRD), thermal gravimetric analysis (TGA), and vibrating sample magnetometer (VSM) measurements. This organometallic catalyst was recovered by the assistance of an external magnetic field from the reaction mixture and reused for seven continuous cycles without noticeable change in its catalytic activity.
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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- Synthesis and characterization of MCM-41@XA@Ni(II) as versatile and heterogeneous catalyst for efficient oxidation of sulfides and acetylation of alcohols under solvent-free conditions
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Herein, Ni(II) immobilized on modified mesoporous silica MCM-41 was designed and synthesized via a facile sequential strategy. The structure of the catalyst was characterized by X-ray diffraction. The thermal property of the as-synthesized materials was studied using thermogravimetric-differential thermal analysis. The average particles size and morphology of MCM-41@XA@Ni(II) were investigated using scanning electron microscopy and transmission electron microscopy. This nanostructure catalyst was effective for the selective oxidation of sulfides and acetylation of alcohols in solvent-free conditions. The easy recyclability of the catalyst and their complete chemoselectivity toward the sulfur group of substrates in the oxidation of sulfides are important “green” attributes of this catalyst.
- Nazarzadeh, Somayeh,Ghorbani-Choghamarani, Arash,Tahanpesar, Elham
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p. 649 - 659
(2018/01/28)
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- Highly efficient, green, rapid, and chemoselective oxidation of sulfur-containing compounds in the presence of an MCM-41@creatinine@M (M = la and Pr) mesostructured catalyst under neat conditions
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In the present study, we report the synthesis of two green recoverable catalysts by covalent linking of the creatinine La and Pr complexes on an MCM-41 mesostructure with the commercially available materials and via a simple and inexpensive procedure. These heterogeneous catalysts were characterized by Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, scanning electron microscopy, N2 adsorption and desorption, inductively coupled plasma optical emission spectroscopy, and thermogravimetric analysis. The obtained mesostructures act as active and reusable catalysts for the oxidation of sulfides and oxidative coupling of thiols under neat conditions. More importantly, significant practical advantages of this environmentally friendly process include high efficiency, good reaction times, and convenient recovery and reusability for several times without any significant loss of activity of the catalyst.
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 5479 - 5488
(2018/03/30)
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- Fe3O4-AMPD-Pd: A novel and efficient magnetic nanocatalyst for synthesis of sulfides and oxidation reactions
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A novel magnetic nanoparticle was synthesized with effective catalytic properties and recyclable ability. This heterogeneous nanocatalyst was identified using Fourier transform infrared, scanning electron microscopies, X‐ray diffraction, vibrating sample magnetometer, inductively coupled plasma atomic emission spectroscopy and thermogravimetric analysis methods. The nanocatalyst was used for the synthesis of the one-pot C–S coupling synthesis of sulfide in the presence of KOH, S8 as the sulfur source in DMSO as the solvent at 100 °C. Also, the oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides in the presence of the catalyst was tested. The catalyst has unique properties such as ability of magnetic separation from the reaction, high repeatability, and high thermal and chemical stability.
- Tamoradi, Taiebeh,Moeini, Nazanin,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 104 - 109
(2018/07/29)
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- Immobilization of a nickel complex onto functionalized Fe3O4 nanoparticles: a green and recyclable catalyst for synthesis of 5-substituted 1H-tetrazoles and oxidation reactions
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Abstract: In the present research, a magnetically recoverable catalyst was easily prepared by anchoring nickel onto the surface of organically modified magnetite nanoparticles. Characterization of the prepared nanostructure was performed by various physico-chemical techniques such as Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, thermal gravimetric analysis and vibrating sample magnetometer measurements. The catalytic behavior of the prepared nanohybrid as an efficient catalyst was successfully probed in the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted 1H-tetrazoles. This method was found to have significant advantages, including high yield, green reaction conditions, short reaction time, easy separation and workup, as well as the ability to tolerate a wide variety of substitutions in the reagents. Graphical Abstract: [Figure not available: see fulltext.].
- Tamoradi, Taiebeh,Mehraban-Esfandiari, Bita,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 1363 - 1380
(2017/10/30)
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- A novel catalytic system poly(1-vinyl-3-dodecylimidazolium tribromide)/TBN for the oxidation of sulfides to sulfoxides with air as oxidant
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A novel and recoverable polymeric ionic liquid, poly(1-vinyl-3-dodecylimidazolium tribromide) (Poly[VDIM]Br3), was successfully prepared and fully characterized. And a highly efficient metal-free catalytic system Poly[VDIM]Br3/tert-butyl nitrite was developed for the oxidation of sulfides. With air as oxidant, we have successfully achieved 19 kinds of sulfides selectively and efficiently oxidized to corresponding sulfoxides using this catalytic system at room temperature.
- Zhang, Hua,Qi, Linlin
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p. 3171 - 3174
(2018/07/13)
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- Anchoring Ni (II) on Fe3O4@tryptophan: A recyclable, green and extremely efficient magnetic nanocatalyst for one-pot synthesis of 5-substituted 1H-tetrazoles and chemoselective oxidation of sulfides and thiols
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A green, novel and extremely efficient nanocatalyst was successfully synthesized by the immobilization of Ni as a transition metal on Fe3O4 nanoparticles coated with tryptophan. This nanostructured material was characterized using Fourier transform infrared spectroscopy, transmission electron microscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, vibrating sample magnetometry and X-ray diffraction. The prepared nanocatalyst was applied for the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted 1H-tetrazoles. The use of non-toxic, green and inexpensive materials, easy separation of magnetic nanoparticles from a reaction mixture using a magnetic field, efficient and one-pot synthesis, and high yields of products are the most important advantages of this nanocatalyst.
- Moeini, Nazanin,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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- Fe3O4@S-ABENZ@VO: Magnetically separable nanocatalyst for the efficient, selective and mild oxidation of sulfides and oxidative coupling of thiols
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Oxovanadium(IV) immobilized on Fe3O4@S-ABEN is reported as a highly efficient nanocatalyst for the oxidation of sulfides and oxidative coupling of thiols (using H2O2 as green oxidant), the products of which are obtained in high to excellent yields. The products can be separated by a simple extraction with organic solvent and the catalyst is highly efficient, especially in terms of selectivity of desired product. The catalytic system can be recycled and reused without significant loss of catalytic activity.
- Rezaei, Somaieh,Ghorbani-Choghamarani, Arash,Badri, Rashid,Nikseresht, Ahmad
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- Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
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Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.
- Gan, Shaoyan,Yin, Junjie,Yao, Yuan,Liu, Yang,Chang, Denghu,Zhu, Dan,Shi, Lei
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supporting information
p. 2647 - 2654
(2017/04/03)
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- Synthesis of Fe3O4@SiO2@DOPisatin-Ni(II) and Cu(II) nanoparticles: Highly efficient catalyst for the synthesis of sulfoxides and disulfides
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The catalytic activity of two magnetic catalysts Fe3O4@SiO2@DOPisatin-M(II) (M?=?Ni, Cu) was investigated in the environmentally green H2O2 oxidant-based oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. By using these catalysts, various substrates were successfully converted into their corresponding product. These catalysts could also be reused multiple time without significant loss of activity. The physical and chemical properties of the catalysts were determined using scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), vibrating sample magnetometer (VSM), energy dispersive X-ray spectroscopy (EDX) and atomic absorption spectroscopy (AAS).
- Hajjami, Maryam,Sharifirad, Fatemeh,Gholamian, Fatemeh
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- Tribromide ion immobilized on magnetic nanoparticles as an efficient catalyst for the rapid and chemoselective oxidation of sulfides to sulfoxides
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Tris(tetraalkyl ammonium tribromide) immobilized on Fe3O4 magnetic nanoparticles (Br3-Fe3O4) is a stable, green, and magnetically recoverable source of bromine and used as an efficient nanocatalyst for the clean and rapid oxidation of sulfides to sulfoxides using hydrogen peroxide (H2O2), with short reaction times in good to high yields under solvent-free conditions. After completing reactions, the catalyst was easily separated using an external magnetic field from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency. The nanomagnetically catalyst was characterized by FT-IR spectroscopy, TGA, VSM, XRD, TEM and SEM.
- Shiri, Lotfi,Tahmasbi, Bahman
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supporting information
p. 53 - 57
(2016/12/24)
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- A magnetically retrievable heterogeneous copper nanocatalyst for the synthesis of 5-substituted tetrazoles and oxidation reactions
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Abstract: A copper complex anchored on functionalized Fe3O4 nanoparticles was prepared by a simple and inexpensive procedure using commercially available materials. The prepared catalyst was characterized by a range of physical and spectroscopic techniques. Ease of operation, high efficiency, eco-friendly procedure, easy separation of the catalyst and reusability for several consecutive runs without significant loss of its activity are several advantages of this catalyst. The catalytic activity has been explored for the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted tetrazoles. Graphical Abstract: A magnetically retrievable heterogeneous copper nanocatalyst for the synthesis of 5-substituted tetrazoles and oxidation reactions[Figure not available: see fulltext.].
- Darabi, Mitra,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 703 - 710
(2017/10/07)
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- Preparation and characterization of oxovanadium(IV)-glycine imine immobilized on magnetic nanoparticles and its catalytic application for selective oxidation of sulfides to sulfoxides
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A novel Fe3O4@VO (salen) complex was designed as an efficient and heterogeneous catalyst for selective oxidation of sulfides to sulfoxides using H2O2 at room temperature. The catalyst was characterized by techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD) analysis, Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), vibrating-sample magnetometry (VSM), and inductively coupled plasma optical emission spectrometry (ICP-OES) analysis. The simple preparation of the catalyst from commercially available materials, excellent chemoselectivity, easy separation of products, and straightforward recovery and reusability of the catalyst with unaltered activity make our procedure a green and practical method.
- Ghorbani-Choghamarani, Arash,Shiri, Lotfi,Azadi, Gouhar
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p. 6049 - 6060
(2016/06/01)
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- Immobilization of a vanadium complex onto functionalized nanoporous MCM-41 and its application as a catalyst for the solvent-free chemoselective oxidation of sulfide to sulfoxide
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A complex moiety containing VO(IV) was anchored covalently into organic-modified Si-MCM-41 to prepare a new catalyst. The prepared materials were characterized using various techniques. Several types of aromatic and aliphatic sulfides were successfully oxidized to the corresponding sulfoxides in good to excellent yields using H2O2 in the presence of a catalytic amount of the catalyst under solvent-free conditions. The results showed that the OH groups of the various compounds such as 2,2-(phenylthio)ethanol and 2-(methylthio)ethanol remained intact under similar conditions. Meanwhile the catalyst was stable in the reaction system, and could be reused at least four times without significant loss of its activity and chemoselectivity.
- Nikoorazm,Ghorbani-Choghamarani,Khanmoradi
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p. 236 - 241
(2016/04/05)
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- Bovine serum albumin-cobalt(II) Schiff base complex hybrid: An efficient artificial metalloenzyme for enantioselective sulfoxidation using hydrogen peroxide
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An artificial metalloenzyme (BSA-CoL) based on the incorporation of a cobalt(ii) Schiff base complex {CoL, H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol} with bovine serum albumin (BSA) has been synthesized and characterized. Attention is focused on the catalytic activity of this artificial metalloenzyme for enantioselective oxidation of a variety of sulfides with H2O2. The influences of parameters such as pH, temperature, and the concentration of catalyst and oxidant on thioanisole as a model are investigated. Under optimum conditions, BSA-CoL as a hybrid biocatalyst is efficient for the enantioselective oxidation of a series of sulfides, producing the corresponding sulfoxides with excellent conversion (up to 100%), chemoselectivity (up to 100%) and good enantiomeric purity (up to 87% ee) in certain cases.
- Tang, Jie,Huang, Fuping,Wei, Yi,Bian, Hedong,Zhang, Wei,Liang, Hong
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p. 8061 - 8072
(2016/06/06)
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- Schiff base complexes of Ni, Co, Cr, Cd and Zn supported on magnetic nanoparticles: As efficient and recyclable catalysts for the oxidation of sulfides and oxidative coupling of thiols
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Abstract Oxidation of sulfides to sulfoxides and oxidative coupling of thiols into their corresponding disulfides were carried out using hydrogen peroxide (H2O2) as oxidizing agent in the presence of immobilized Ni, Co, Cr, Zn or Cd complexes on Fe3O4 magnetic nanoparticles (M-Salen-MNPs) as stable, heterogeneous, efficient and magnetically recoverable nanocatalysts under mild reaction conditions. These supported complexes were characterized by FT-IR spectroscopy, thermogravimetric analysis (TGA), powder X-ray diffraction (XRD), scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDS). A variety of aromatic and aliphatic sulfides and thiols with different functional groups were successfully oxidized with short reaction times in good to excellent yields. Recovery of the catalyst is easily achieved by magnetic decantation and reused for several consecutive runs without significant loss of its catalytic efficiency.
- Ghorbani-Choghamarani, Arash,Darvishnejad, Zahra,Tahmasbi, Bahman
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p. 223 - 231
(2015/08/03)
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- Mild, Selective, and Efficient Oxidation of Sulfides to Sulfoxides Catalyzed by Mn(III)-Salen Complexes
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A detailed optimization of the catalytic environment for the oxidation of sulfides promoted by Mn(salen)/H2O2 systems is proposed. The experimental setup is demonstrated to be active towards different substrates, providing TOFs up to 9300 h-1, which are among the highest reported for homogeneous catalysts employed in sulfoxidation reactions.
- Bismuto, Alessandro,Cucciolito, Maria E.,Ruffo, Francesco,Vitagliano, Aldo,Curcio, Massimiliano
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p. 1021 - 1028
(2015/08/04)
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- Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine
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An efficient and practical catalytic method for the aerobic oxidative transformation of sulfides into sulfoxides, and thiols into disulfides with formic acid/TEA in the presence of a new, readily available, and stable flavin catalyst 5d is described. This journal is the Partner Organisations 2014.
- Murahashi, Shun-Ichi,Zhang, Dazhi,Iida, Hiroki,Miyawaki, Toshio,Uenaka, Masaaki,Murano, Kenji,Meguro, Kanji
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supporting information
p. 10295 - 10298
(2014/08/18)
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- Palladium on carbon-catalyzed gentle and quantitative combustion of hydrogen at room temperature
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A quantitative and gentle oxidation (combustion) of hydrogen in the presence of oxygen in a variety of solvents was achieved under palladium on carbon (Pd/C)-catalyzed conditions at ordinary pressures and temperatures. A quantitative generation of water accountable for the consumed oxygen was observed. While hydrogen peroxide (H2O2), which would form as an intermediate, was extremely unstable under the Pd/C-catalyzed conditions to be converted into water with accompanying oxygen generation, the stability of H2O2 was found to be increased in cold (0 °C) trifluoroacetic acid, and the formation of 64% H2O2 based on the consumed oxygen could be detected. A mechanistic elucidation study revealed that the single electron transfer and generation of the hydroxyl radical are involved in the gentle combustion process. The reactive oxygen species generated during the process was effectively utilized for the chemical oxidation of sulfides and phosphines to afford the corresponding sulfoxides and phosphine oxides, respectively.
- Monguchi, Yasunari,Ida, Takashi,Maejima, Toshihide,Yanase, Takayoshi,Sawama, Yoshinari,Sasai, Yasushi,Kondo, Shin-Ichi,Sajiki, Hironao
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supporting information
p. 313 - 318
(2014/05/20)
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- Activation of H2O2 by chiral confined Bronsted acids: A highly enantioselective catalytic sulfoxidation
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Confined chiral Bronsted acids are shown to catalyze asymmetric oxidations of sulfides to sulfoxides with hydrogen peroxide. The wide generality and high enantioselectivity of the developed method compare even to the best metal-based systems and suggest utility in other asymmetric oxidations.
- Liao, Saihu,Coric, Ilija,Wang, Qinggang,List, Benjamin
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supporting information; experimental part
p. 10765 - 10768
(2012/08/28)
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- Flavin-cyclodextrin conjugates: Effect of the structure on the catalytic activity in enantioselective sulfoxidations
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A series of flavin-cyclodextrin conjugates has been prepared and tested in the enantioselective oxidations of prochiral aromatic and aliphatic sulfides with hydrogen peroxide. The newly prepared conjugates contain isoalloxazinium or alloxazinium moieties attached to the primary rim of α- and β-cyclodextrins at the C-6 positions. In addition, flavinium units were attached to the secondary rim of the β-cyclodextrin macrocycle. The relationship between the structural features and the catalytic performance of the conjugates, including those recently reported by us, was analyzed. The rate and enantioselectivity of the sulfoxidations catalyzed by flavin-cyclodextrin conjugates are influenced mainly by the size of the cyclodextrin cavity, the type of flavin unit (alloxazine or isoalloxazine), and by the relative orientation of the flavin and cyclodextrin moieties.
- Hartman, Tomas,Herzig, Vladimir,Budesinsky, Milos,Jindrich, Jindrich,Cibulka, Radek,Kraus, Tomas
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p. 1571 - 1583
(2013/02/23)
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- Alloxazine-cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations
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Four structurally different alloxazine-cyclodextrin conjugates were prepared and tested as catalysts for the enantioselective oxidation of prochiral sulfides to sulfoxides by hydrogen peroxide in aqueous solutions. The alloxazinium unit was appended to the primary face of α- and β-cyclodextrins via a linker with variable length. A series of sulfides was used as substrates: n-alkyl methyl sulfides (n-alkyl = hexyl, octyl, decyl, dodecyl), cyclohexyl methyl sulfide, tert-butyl methyl sulfide, benzyl methyl sulfide and thioanisol. α-Cyclodextrin conjugate having alloxazinium unit attached via a short linker proved to be a suitable catalyst for oxidations of n-alkyl methyl sulfides, displaying conversions up to 98% and enantioselectivities up to 77% ee. β-Cyclodextrin conjugates were optimal catalysts for the oxidation of sulfides carrying bulkier substituents; e.g. tert-butyl methyl sulfide was oxidized with quantitative conversion and 91% ee. Low loadings (0.3-5 mol%) of the catalysts were used. No overoxidation to sulfones was observed in this study.
- Mojr, Viktor,Budesinsky, Milos,Cibulka, Radek,Kraus, Tomas
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experimental part
p. 7318 - 7326
(2011/12/03)
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- New odorless method for the Corey-Kim and Swern oxidations utilizing dodecyl methyl sulfide (Dod-S-Me)
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Development of the odorless dodecyl methyl sulfide (Dod-S-Me, 1) as an alternative for dimethyl sulfide (DMS) and new odorless methods for the Corey-Kim and Swern oxidations are described. These reactions have been developed with a view toward green chemistry, utilizing Dod-S-Me (1) and common solvents instead of dichloromethane.
- Ohsugi, Shin-Ichi,Nishide, Kiyoharu,Oono, Keiji,Okuyama, Kazunori,Fudesaka, Masato,Kodama, Sumiaki,Node, Manabu
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p. 8393 - 8398
(2007/10/03)
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- Tungstate-exchanged Mg-Al-LDH catalyst: An eco-compatible route for the oxidation of sulfides in aqueous medium
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The catalytic oxidation of sulfides selectively to sulfoxides and/or sulfones is realised for the first time with heterogeneous tungstate-exchanged Mg-Al-LDH catalyst using 30% hydrogen peroxide in aqueous media at a faster rate in quantitative yields at room temperature. The heterogeneous catalyst showed higher activity (TOF) over its homogeneous analogues and other heterogeneous catalysts reported so far. The catalyst is well characterised by various instrumental techniques such as FT-IR spectroscopy, thermal analysis (TGA and DTA), powder XRD and chemical analysis. The catalyst is reused for six cycles with consistent activity and selectivity.
- Choudary,Bharathi,Venkat Reddy,Lakshmi Kantam
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p. 2069 - 2074
(2007/10/03)
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- Microwave thermolysis with clayfen: Solvent-free oxidation of sulfides to sulfoxides
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Alkyl, aryl and cyclic sulfides are rapidly oxidized to the corresponding sulfoxides in high yields upon microwave thermolysis with iron(III) nitrate impregnated on clay (clayfen) under solvent-free conditions; the conversion also occurs in refluxing methylene chloride but requires much longer reaction time.
- Varma, Rajender S.,Dahiya, Rajender
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p. 4087 - 4095
(2007/10/03)
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- Selective Oxidations using Alumina-supported Iodobenzene Diacetate under Solvent-free Conditions
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The solid reagent system iodobenzene diacetate-alumina expeditiously and selectively oxidises Sulfides to sulfoxides and alcohols to carbonyl compounds in high yields under the influence of microwaves.
- Varma, Rajender S.,Saini, Rajesh K.,Dahiya, Rajender
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p. 120 - 121
(2007/10/03)
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- Selective oxidation of sulfides to sulfoxides and sulfones by microwave thermolysis on wet silica-supported sodium periodates
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A variety of symmetrical and unsymmetrical sulfides have been selectively and expeditiously oxidized to either sulfoxides or sulfones in good yields using wet silica-supported sodium periodate under microwave thermolysis conditions.
- Varma, Rajender S.,Saini, Rajesh K.,Meshram, Harshadas M.
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p. 6525 - 6528
(2007/10/03)
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- Enantio- and Diastereoselectivity in the Periodate Oxidation of Sulfides Catalyzed by Bovine Serum Albumin. 2
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The asymmetric oxidation of aliphatic, aromatic, and heterocyclic sulfides in the presence of a catalytic amount of bovine serum albumin (BSA) affords the corresponding sulfoxides with enantiomeric excess (ee) up to 80percent.The diastereoselectivity of the process has also been examined in comparison with the enzymatic oxygenation with cytochrome P-450.Electronic and CD spectral data indicate that the sulfides are not tightly bound to BSA in the reaction conditions.
- Colonna, Stefano,Banfi, Stefano,Annunziata, Rita,Casella, Luigi
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p. 891 - 895
(2007/10/02)
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