- β-CYCLODEXTRIN PHOSPHATE. A REMARKABLE CATALYST FOR THE IODINE OXIDATION OF BENZYL METHYL SULFIDE TO THE SULFOXIDE IN WATER
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β-Cyclodextrin phosphate has been found to be a remarkable catalyst for the iodine oxidation of benzyl methyl sulfide to the sulfoxide in water.
- Eiki, Toshio,Tagaki, Waichiro
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- Efficient, selective and mild oxidation of sulfides and oxidative coupling of thiols catalyzed by Pd(II)-isatin Schiff base complex immobilized into three-dimensional mesoporous silica KIT-6
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In this study, a palladium(II)-isatin Schiff base complex immobilized into three-dimensional (3D) mesoporous silica KIT-6 (Pd-isatin Schiff base@KIT-6) was synthesized and characterized by various techniques including inductively coupled plasma (ICP) and
- Pakvojoud, Saeedeh,Hatefi Ardakani, Mehdi,Saeednia, Samira,Heydari-Bafrooei, Esmaeil
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- A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
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A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
- Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
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supporting information
p. 156 - 161
(2021/01/14)
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- Green synthesis of Cu/Fe3O4nanocomposite using Calendula extract and evaluation of its catalytic activity for chemoselective oxidation of sulfides to sulfoxides with aqueous hydrogen peroxide
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Plant mediated biogenic synthesizednanoparticles have beenquite familiar as next generation prospective catalysts. In this work, we have demonstrated copper nanoparticles (Cu NP) immobilized magnetic Fe3O4 nanoparticles using Calendu
- Ansari, Siddique Akber,Elgorban, Abdallah M.,Marraiki, Najat,Syed, Asad
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- Green synthesis of gold nanoparticles (Au NPs) using Tribulus terrestris extract: Investigation of its catalytic activity in the oxidation of sulfides to sulfoxides and study of its anti-acute leukemia activity
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With regards to applied, facile, green chemical research, a bio-inspired approach is being reported for the synthesis of Au NPs by using Tribulus terrestris extract. The innate oxygenated phytochemicals facilitated the green reduction of Au3+ ions to corresponding NPs and also stabilized them by encapsulating them. This modification prevented the as-synthesized Au NPs towards agglomeration and tiny NPs were obtained in uniformly spherical in shape and in the range of 10–15 nm dimension. Physicochemical characteristics of the green synthesized Au NPs were evaluated by advanced physicochemical techniques like UV–Vis and FT-IR spectroscopy, SEM, TEM, EDX and XRD study. Catalytic performance of the biomolecule functionalized Au NPs was investigated in the controlled and selective oxidation of sulfides to sulfoxides using hydrogen peroxide as green oxidant at room temperature. Aromatic, aliphatic and heterocyclic sulfides were oxidized to their corresponding sulfoxides with high yields without formation of over oxidized sulfones. The catalyst was easily recovered and recycled for 8 successive times without noticeable decrease in catalytic activity. In addition, the biosynthesized Au NPs indicated suitable antioxidant and anti-acute leukemia properties against THP-1 cell line. Tribulus terrestris extract and the green synthesized Au NPs exhibited a maximum DPPH scavenging activity of 78% and 29.37%, respectively. Again, in the anticancer studies over THP-1 cell line following MTT assay, the Au NP exhibited gradual reduced % cell viability with increase in its concentration. At an Au NPs concentration of 2000 μg/mL, the % toxicity became maximum suggesting efficient inhibition of cancer invasion. Based on the above results, Au NPs-Tribulus could be administered as a potential anti-leukemia drug for the treatment of acute leukemia following the clinical trial studies in humans.
- Ahmed, Ahmed Ezzat,El-kott, Attalla,Khames, Ahmed,Zein, Mohamed Abdellatif,Zhao, Peng
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- Oxo-vanadium(IV) unsymmetrical Schiff base complex immobilized on γ-Fe2O3 nanoparticles: A novel and magnetically recoverable nanocatalyst for selective oxidation of sulfides and oxidative coupling of thiols
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In this research, an unsymmetrical salen-type oxo-vanadium(IV) complex, [VO(salenac-OH)] (salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4-methylnona-2,4,8-trienato](-2)), was synthesized and covalently immobilized on the surface of magnetic γ-Fe2
- Mahdian, Abolfazl,Ardakani, Mehdi Hatefi,Heydari-Bafrooei, Esmaeil,Saeednia, Samira
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- Fabrication of molybdenum-substituted tungstophosphoric acid immobilized onto functionalized graphene oxide: Visible light-induced photocatalyst for selective oxidation of sulfides to sulfoxides
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Three set of molybdenum-substituted tungstophosphoric acid (H3PW12-yMoyO40 and y = 0, 6 and 12) was supported onto ethylene diamin functionalized magnetic graphene oxide (EDMG) and used to catalyze the selective
- Fakhri, Hanieh,Mahjoub, Alireza,Maridiroosi, Anasheh,Nejat, Razieh
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- Organocatalytic sulfoxidation
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Treatment of a sulfide with a catalytic amount of a 1,3-diketone in the presence of silica sulfuric acid as a co-catalyst and hydrogen peroxide (50% aq) as the stoichiometric oxidant leads to the corresponding sulfoxide product. The reaction is effective for diaryl, aryl-alkyl and dialkyl sulfides and is tolerant of oxidisable and acid sensitive functional groups. Investigations have shown that the tris-peroxide 2, formed on reaction of pentane-2,4-dione with hydrogen peroxide under acidic reaction conditions, can oxidise two equivalents of sulfide using the exocyclic peroxide groups whereas the endocyclic peroxide remains intact. Calculations provide a mechanism consistent with experimental observations and suggest the reaction proceeds via an initial acid catalysed ring opening of a protonated tris-peroxide prior to oxygen transfer to a sulfur nucleophile.
- Davidson, Stuart C.,Gomes, Gabriel dos Passos,Kuhn, Leah R.,Alabugin, Igor V.,Kennedy, Alan R.,Tomkinson, Nicholas C.O.
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- Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide
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A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO has been developed. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.
- Fu, Duo,Dong, Jun,Du, Hongguang,Xu, Jiaxi
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p. 2752 - 2758
(2020/01/31)
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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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- 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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- An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor
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A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.
- Laudadio, Gabriele,Straathof, Natan J. W.,Lanting, Menno D.,Knoops, Benny,Hessel, Volker,No?l, Timothy
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supporting information
p. 4061 - 4066
(2017/09/07)
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- Green Organocatalytic Oxidation of Sulfides to Sulfoxides and Sulfones
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A highly efficient synthetic methodology towards the selective synthesis of sulfoxides and sulfones is reported using a cheap and green organocatalytic method. Starting from sulfides and using 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, the high-yielding preparation of sulfoxides or sulfones is described, being dependent on the reaction conditions.
- Voutyritsa, Errika,Triandafillidi, Ierasia,Kokotos, Christoforos G.
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p. 917 - 924
(2017/02/15)
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- Stereoselective sulfoxidation catalyzed by achiral Schiff base complexes in the presence of serum albumin in aqueous media
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Four coordination complexes ML derived from an achiral Schiff base ligand (H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol) have been synthesized and characterized. A method is described for the enantioselective oxidation of a series of aryl alkyl sulfides using the coordination complexes in the presence of serum albumins (SAs) in an aqueous medium at ambient temperature. The mixture of metal complexes with serum albumins is useful for inducing asymmetric catalysis. The complex, albumin source and substrate influence stereoselective sulfoxidation. At optimal pH with the appropriate oxidant, some of ML/SA systems are identified as very efficient catalysts, giving the corresponding sulfoxides in excellent chemical yield (up to 100%) and good enantioselectivity (up to 94% ee) in certain cases. UV–visible spectroscopic data provide evidence that stronger binding between the complex and serum albumin lead to higher enantioselectivity.
- Tang, Jie,Yao, Pengfei,Huang, Fuping,Luo, Meiyi,Wei, Yi,Bian, Hedong
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p. 1700 - 1707
(2017/11/17)
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- Photoredox catalysis for oxygenation/deoxygenation between sulfides and sulfoxides by visible-light-responsive polyoxometalates
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In this paper, we report the unique visible-light-responsive photoredox catalysis of a divacant lacunary silicotungstate TBA4H4[γ-SiW10O36] (SiW10) for functional group transformations of sulfur-containing compounds; namely, (i) aerobic oxygenation of sulfides to sulfoxides and (ii) deoxygenation of sulfoxides to sulfides. In the presence of suitable additives, such as Ce3+ (electron transfer mediator for oxygenation) and an alcohol (electron and proton donor for deoxygenation), SiW10 shows visible-light-induced charge transfers by using the newly formed highest occupied molecular orbitals derived from the coordinating Ce3+ or alcohol at the vacant site of SiW10. Consequently, oxygenation of sulfides and deoxygenation of sulfoxides can selectively proceed by irradiation with visible light (λ > 400 nm) to afford the corresponding desired products in high yields. The SiW10 photocatalysts can readily be recovered and reused for these transformations. Based on evidence from several experiments, the roles of the additives as well as the reaction mechanisms for these transformations are also discussed.
- Suzuki, Kosuke,Jeong, Jinu,Yamaguchi, Kazuya,Mizuno, Noritaka
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p. 1014 - 1021
(2016/02/19)
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- New metal complexes supported on Fe3O4 magnetic nanoparticles as recoverable catalysts for selective oxidation of sulfides to sulfoxides
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Fe3O4 nanoparticles were coated with aminopropyltriethoxysilane and subsequently reacted with isatin to obtain imine-bonded Fe3O4 nanoparticles. The addition of ZrOCl2·8H2O or CuCl2 led to the formation of complexes of Zr(IV)/isatin@Fe3O4 or Cu (II)/isatin@Fe3O4 as new magnetically separable catalysts. The synthesized catalysts were characterized using various techniques. These catalysts are shown to be efficient for chemo-selective oxidation of sulfides to sulfoxides using hydrogen peroxide as oxidative agent. This system has many advantages, such as excellent level of reusability of magnetic catalysts, high yields, simplicity of separation of catalysts using an external magnet, environmental benignity and ease of handling.
- Hajjami, Maryam,Kolivand, Somaye
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p. 282 - 288
(2016/05/02)
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- Synthesis and characterization of Co (II) and Fe (III) Schiff base complexes grafted onto mesoporous MCM-41: A heterogeneous and recyclable nanocatalysts for the selective oxidation of sulfides and oxidative coupling of thiols
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Novel organic–inorganic hybrid heterogeneous catalysts containing cobalt(II) and iron(III) Schiff base complexes, grafted on the internal surface of MCM-41 pores were prepared by introducing a metal salt into a mesoporous silica functionalized with a Schiff base ligand. The chemical and physical properties of the catalysts were investigated by BET, TGA, XRD, FT-IR, and TEM techniques. These complexes were found to be efficient, selective catalysts for the oxidation of various sulfides to sulfoxides and oxidative coupling of thiols to their corresponding disulfides with urea hydrogen peroxide in excellent yield at room temperature. The designed catalytic system prevents effectively the overoxidation of sulfides and thiols to sulfoxides and sulfones, respectively. Also the heterogeneous catalysts can be recovered easily and reused many times without significant loss of activity and selectivity.
- Noori, Nourolah,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
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p. 1388 - 1395
(2016/09/28)
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- Synthesis, characterization, and catalytic application of Cr and Mn Schiff base complexes immobilized on modified nanoporous MCM-41
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Immobilization of chromium and manganese Schiff base complexes by postgrafting of ligand then metal salts on the walls of mesoporous MCM-41 functionalized with (3-aminopropyl)triethoxysilane is described. Characterization of the resulting heterogeneous catalysts by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), transmission electron microscopy (TEM), X-ray diffraction (XRD) analysis, and Brunauer–Emmett–Teller (BET) techniques indicated successful grafting of these two complexes inside the nanochannels of MCM-41. The complexes were found to be efficient, selective catalysts for oxidation of various sulfides to sulfoxides and oxidative coupling of thiols to corresponding disulfides using H2O2 as oxidant at room temperature. The recycling results of these heterogeneous catalysts showed good recyclability without significant loss of activity or selectivity in successive runs, indicating that the Cr and Mn Schiff base complexes supported on nanoporous MCM-41 remained intact and the coordination environments were not altered during the reaction.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Noori, Nourolah
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p. 4621 - 4640
(2016/07/06)
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- Preparation of DSA@MNPs and application as heterogeneous and recyclable nanocatalyst for oxidation of sulfides and oxidative coupling of thiols
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Abstract: Dopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (DSA@MNPs) were prepared by a very simple and inexpensive procedure using commercial materials and characterized by X-ray diffraction (XRD) analysis, thermogravimetric analysis (TGA), Fourier-transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and vibrating-sample magnetometry (VSM) techniques. They were employed as an efficient and recoverable catalyst in oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides using hydrogen peroxide as green oxidant at room temperature. This is the first report of application of DSA@MNPs in organic reactions. The supported magnetic nanoparticles could be easily recovered using an appropriate external magnet, minimizing catalyst loss during separation, and reused for several times without any loss of catalytic activity. Also, the amount of sulfamic acid function in the DSA@MNPs was calculated from ion-exchange pH analysis and back titration. Graphical abstract: [Figure not available: see fulltext.]
- Ghorbani-Choghamarani, Arash,Rabiei, Hossein,Tahmasbi, Bahman,Ghasemi, Banoo,Mardi, Farideh
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p. 5723 - 5737
(2016/06/01)
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- Efficient Metal-Free Aerobic Photooxidation of Sulfides to Sulfoxides Mediated by a Vitamin B2Derivative and Visible Light
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We have developed a metal-free process for the aerobic photooxygenation of sulfides to sulfoxides mediated by riboflavin tetraacetate or riboflavin (vitamin B2) photocatalysts and visible light (450 nm) in an acetonitrile-water (85:15 v/v) mixture. The optimised solvent system leads to both singlet-oxygen and electron-transfer pathways in photooxygenation, thus allowing oxidation of electron-poor and electron-rich thioanisoles, dialkyl sulfides and sterically hindered sulfides. Besides having a broad substrate scope, the method has very short reaction times and requires low catalyst loading (down to 0.1 mol%). These properties are due to the high photocatalyst stability and the extremely high quantum yields (1.3 for thioanisole oxygenation). Moreover, the method is chemoselective, producing only sulfoxides without overoxidation to sulfones. Taking into account the broad substrate scope, high selectivity and high efficiency, this method distinguishes itself from those previously reported. Other advantages include easy work-up of the reaction mixture, the availability and biodegradability of the photocatalysts and mild reaction conditions. We demonstrated, on a preparative scale, its practical application in the synthesis of the psychostimulant modafinil, in the selective oxidation of methionine derivatives, and in the detoxification of mustard gas. (Figure presented.).
- Nevesely, Tomá?,Svobodová, Eva,Chudoba, Josef,Sikorski, Marek,Cibulka, Radek
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p. 1654 - 1663
(2016/10/13)
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- Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: Rhodium-catalyzed double C-H activation controlled by different directing groups
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A rhodium(III)-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (C-H, C-S, O-H) and the formation of two bonds (C-C, C-O). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double C-H activation, the first of such examples in cross-oxidative coupling.
- Zhang, Xi-Sha,Zhang, Yun-Fei,Li, Zhao-Wei,Luo, Fei-Xian,Shi, Zhang-Jie
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p. 5478 - 5482
(2015/04/27)
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- Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide
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An easily accessible polyoxomolybdate-calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes-polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.
- Meninno, Sara,Parrella, Alessandro,Brancatelli, Giovanna,Geremia, Silvano,Gaeta, Carmine,Talotta, Carmen,Neri, Placido,Lattanzi, Alessandra
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supporting information
p. 5100 - 5103
(2015/11/03)
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- Schiff base complex coated Fe3O4 nanoparticles: A highly reusable nanocatalyst for the selective oxidation of sulfides and oxidative coupling of thiols
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In this work, a new nanomagnetic complex of Cu(II) has been synthesized. The prepared catalyst was characterized by TG/DTG, FT-IR, TEM, VSM, ICP, AAS, XRD, EDS and SEM analyses. It was found to be an efficient catalyst for the oxidation of sulfides and oxidative coupling of thiols. High catalytic activity, ease of recovery from the reaction mixture using an external magnet, and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system.
- Ghorbani-Choghamarani, Arash,Ghasemi, Banoo,Safari, Zohre,Azadi, Gouhar
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- Salen copper(II) complex heterogenized on mesoporous MCM-41 as nano-reactor catalyst for the selective oxidation of sulfides using urea hydrogen peroxide (UHP)
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MCM-41 silica spheres were synthesized and functionalized with 3-aminopropyltriethoxysilane (3-APTES). The Schiff base has been derived from amino groups and 5-boromo salicylaldehyde, then a tetra dentate Cu(II)-Schiff base complex was prepared. This comp
- Jabbari, Arida,Mahdavi, Houri,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
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p. 5649 - 5663
(2015/07/08)
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- Oxo-vanadium(IV) Schiff base complex supported on modified MCM-41: A reusable and efficient catalyst for the oxidation of sulfides and oxidative S-S coupling of thiols
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Oxo-vanadium(IV) Schiff base complex supported on MCM-41 as an organic-inorganic hybrid heterogeneous catalyst was synthesized with post-grafting of MCM-41 with 3-aminoropropyltrimethoxysilane and subsequent reaction with 3,4-dihydroxybenzaldehyde and then complexation with oxo-vanadium acetylacetonate salt. The catalyst was analysed using a series of characterization techniques such as Fourier transform infrared spectroscopy, small-angle X-ray diffraction, nitrogen absorption isotherm, transmission electron microscopy and thermogravimetric analysis. The data collected provided evidence that the vanadium complex was anchored onto MCM-41. High catalytic activity of this catalyst was observed in the oxidation of various sulfides and thiols (into sulfoxides and disulfides, respectively) with urea hydrogen peroxide as oxidant in high to excellent yields and selectivity under mild conditions. The heterogeneous catalyst could be recovered easily and reused several times without significant loss in catalytic activity and selectivity.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Noori, Nourolah
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p. 328 - 333
(2015/04/27)
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- Zirconium oxide complex-functionalized MCM-41 nanostructure: An efficient and reusable mesoporous catalyst for oxidation of sulfides and oxidative coupling of thiols using hydrogen peroxide
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Zirconium oxide complex-functionalized mesoporous MCM-41 (Zr-oxide@MCM-41) as an efficient and reusable catalyst is reported for the oxidation of sulfides into sulfoxides using hydrogen peroxide (H2O2) as the oxidant, with short reaction times in good to excellent yields at room temperature under solvent-free conditions. Also, a simple and efficient method is reported for the oxidative coupling of thiols into corresponding disulfides in good to high yields using H2O2 as oxidant in the presence of Zr-oxide@MCM-41 as recoverable catalyst in ethanol at room temperature. A series of sulfides and thiols possessing functional groups was successfully converted into corresponding products. After completion of reactions the catalyst was easily separated with simple filtration from the reaction mixture and reused for several consecutive runs without significant loss of catalytic efficiency. The mesoporous catalyst was characterized using Fourier transform infrared spectroscopy, Brunauer-Emmett-Teller surface area measurements, X-ray diffraction, transmission and scanning electron microscopies, energy-dispersive X-ray spectroscopy and thermogravimetric analysis.
- Hajjami, Maryam,Shiri, Lotfi,Jahanbakhshi, Azar
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p. 668 - 673
(2015/09/28)
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- Efficient Oxidation of Sulfides to Sulfoxides and Deoxygenation of Sulfoxides over Carbonaceous Solid Acid
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Carbonaceous Solid Acid (CSA) was found to be a highly efficient, environmentally friendly, recyclable heterogeneous solid acid for the oxidation of sulfides and deoxygenation of sulfoxides, in good to excellent yields under mild reaction conditions.
- Atabaki, Fariborz,Abedini, Ebrahim,Shokrolahi, Arash
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p. 1169 - 1176
(2015/08/04)
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- Preparation and characterization of organically modified MCM-48 as heterogonous catalyst for oxidation of sulfides and thiols
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MCM-48 mesoporous synthesized and grafted with aminopropyl triethoxysilane (APTES) and subsequently reacted by isatin to obtain the imine of MCM-48. Addition of ZrOCl2.8H2O, leading to form the complex of Zr(IV)/isatin-MCM-48 as new Schiff base complex of zirconium(IV)-modified-MCM-48. The synthesized catalyst was characterized by XRD, TGA, FT-IR and BET. The resulting catalyst was efficient for selective oxidation of sulfides to sulfoxides and oxidation of thiols to disulfides with hydrogen peroxide. In this method isolation and reusability of catalyst have been investigated.
- Hajjami, Maryam,Yousofvand, Zakieh
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p. 1733 - 1740
(2019/11/28)
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- Efficient preparation of Zr(IV)-salen grafted mesoporous MCM-41 catalyst for chemoselective oxidation of sulfides to sulfoxides and Knoevenagel condensation reactions
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Zr(IV)-salen-MCM-41 was prepared by reaction of NH2-MCM-41 with salicylaldehyde to afford Schiff base ligands. Thereafter, ZrOCl2·8H2O was reacted with the Schiff base ligands for complex formation. The structural properti
- Hajjami, Maryam,Ghorbani, Farshid,Rahimipanah, Sedighe,Roshani, Safoora
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p. 1852 - 1860
(2015/11/17)
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- Selective Synthesis of Sulfoxides through Oxidation of Sulfides with Sodium Hypochlorite Pentahydrate Crystals
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Oxidation of sulfides with sodium hypochlorite pentahydrate crystals (1.1 equiv) in an aqueous acetonitrile solution selectively produces the corresponding sulfoxides in high yields. This procedure is catalyst-free and environmentally benign.
- Okada, Tomohide,Matsumuro, Hiroaki,Kitagawa, Saori,Iwai, Toshiaki,Yamazaki, Kento,Kinoshita, Yukari,Kimura, Yoshikazu,Kirihara, Masayuki
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p. 2547 - 2552
(2015/11/16)
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- Palladium(II)-catalyzed ortho -olefination of arenes applying sulfoxides as remote directing groups
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A novel palladium-catalyzed ortho-C(sp2)-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.
- Wang, Binjie,Shen, Chuang,Yao, Jinzhong,Yin, Hong,Zhang, Yuhong
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- Cu(II)-Schiff base complex-functionalized magnetic Fe3O4 nanoparticles: A heterogeneous catalyst for various oxidation reactions
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Cu(II)-Schiff base complex-functionalized magnetic Fe3O4 nanoparticles were prepared and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis and scanning electron microscopy techniques. This compound acts as a highly active and selective catalyst for the oxidation of sulfides and thiols. These reactions can be carried out in ethanol or solvent-free conditions in the presence of hydrogen peroxide with complete selectivity and very high conversion under mild reaction conditions. The designed catalytic system prevents effectively the over-oxidation of sulfides to sulfones. Separation and recycling can also be easily done using a simple magnetic separation process.
- Ghorbani-Choghamarani, Arash,Darvishnejad, Zahra,Norouzi, Masoomeh
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p. 170 - 175
(2015/03/30)
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- Practical and versatile oxidation of sulfides into sulfoxides and oxidative coupling of thiols using polyvinylpolypyrrolidonium tribromide
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A simple and highly selective oxidation of sulfides to sulfoxides and an oxidative coupling of thiols with polyvinylpolypyrrolidoniume tribromide has been developed. A series of sulfides and thiols was oxidized selectively at room temperature in good to excellent yields.
- Ghorbani-Choghamarani, Arash,Azadi, Gouhar,Tahmasbi, Bahman,Hadizadeh-Hafshejani, Mojtaba,Abdi, Zainab
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p. 433 - 439
(2014/04/03)
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- Selective oxidation of sulfides to sulfoxides by a molybdate-based catalyst using 30% hydrogen peroxide
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An efficient method is reported for selective oxidation of various types of sulfides to sulfoxides and sulfones in good to high yields using 30% H 2O2 in the presence of catalytic amounts of molybdate-based catalyst in acetonitrile as solvent at room temperature. The catalyst can be easily recovered and reused for seven reaction cycles without considerable loss of activity.
- Bayat, Ahmad,Shakourian-Fard, Mehdi,Hashemi, Mohammad Mahmoodi
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- Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides
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The palladium-catalyzed α-arylation of unactivated sulfoxides has been developed. The weakly acidic α-protons of sulfoxides are reversibly deprotonated by LiOtBu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under the optimized conditions. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.
- Jia, Tiezheng,Bellomo, Ana,Baina, Kawtar El,Dreher, Spencer D.,Walsh, Patrick J.
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supporting information
p. 3740 - 3743
(2013/04/10)
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- Magnetic nanoparticle immobilized N-propylsulfamic acid: The chemoselective, efficient, green and reusable nanocatalyst for oxidation of sulfides to sulfoxides using H2O2 under solvent-free conditions
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An efficient and eco-friendly method is reported for the chemoselective oxidation of sulfides to sulfoxides in good to high yields using 30% H 2O2 in the presence of catalytic amounts of N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) under solvent-free conditions at room temperature. Various types of aromatic and aliphatic sulfides possessing functional groups such as alcohol, ester, and aldehyde are successfully and selectively oxidized without affecting sensitive functionalities. The magnetic nanocatalyst can be readily recovered easily by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity.
- Rostami, Amin,Tahmasbi, Bahman,Abedi, Fatemeh,Shokri, Zahra
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p. 200 - 205
(2013/08/23)
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- Selective oxidation of sulfides to sulfoxides using H 2O 2 catalyzed by p-toluenesulfonic acid (p-TsOH) under solvent-free conditions
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An efficient, chemoselective, and environmental friendly procedure for the oxidation of sulfides to sulfoxides is described. Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides in good to excellent yields using 30% H2O2 in the presence of catalytic amounts of a p-TsOH under solvent-free conditions at room temperature.
- Rostami, Amin,Hassanian, Fatemeh,Ghorbani-Choghamarani, Arash,Saadati, Shaghayegh
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p. 833 - 838
(2013/08/23)
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- Sulfoxidation on a SiO2-supported Ru complex using O 2/aldehyde system
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A site-isolated SiO2-supported Ru-monomer complex, whose structure was characterized by means of solid-state NMR, XPS, UV/vis, and Ru K-edge EXAFS, was found to be efficient for sulfoxidation using an O 2/aldehyde system. Significant enhancement of sulfoxidation rates was observed on the SiO2-supported Ru complex for various sulfide derivatives.
- Maity, Niladri,Wattanakit, Chularat,Muratsugu, Satoshi,Ishiguro, Nozomu,Yang, Yong,Ohkoshi, Shin-Ichi,Tada, Mizuki
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supporting information; experimental part
p. 4558 - 4565
(2012/07/02)
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- Biphasic oxidation of sulfides with hydrogen peroxide, catalyzed by partially water-soluble cationic salphen complex
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Sulfides were selectively oxidized to the corresponding sulfoxides or sulfones in good yields by hydrogen peroxide using a partially water-soluble cationic manganese(III)-salphen complex as an efficient phase transfer catalyst for chemoselective oxidation, under mild conditions. The experimental data show that the cationic salt is more active than its neutral form. The acceleration of the reaction rate is attributed to the phase transfer capability of the built-in phenazinium salt of the Mn(III)- salphen catalyst. Iranian Chemical Society 2012.
- Abdolmaleki, Amir,Malek-Ahmadi, Saeed
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p. 1015 - 1019
(2013/02/25)
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- Cyclic seleninate esters as catalysts for the oxidation of sulfides to sulfoxides, epoxidation of alkenes, and conversion of enamines to α-hydroxyketones
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Cyclic seleninate esters serve as catalysts for the rapid oxidation of sulfides to sulfoxides, alkenes to epoxides, and enamines to α-hydroxyketones. Optimal conditions were found that minimize the overoxidation of the product sulfoxides to sulfones and the hydrolysis of epoxides to diols. In some examples such as styrene derivatives, oxidative cleavage was observed instead of epoxidation. The enamine oxidations proceed via the initial formation of dimeric 2,5-diamino-1,4-dioxane species, which were hydrolyzed in situ to the final products. The structure of one such dimer was confirmed by X-ray crystallography.
- Mercier, Eric A.,Smith, Chris D.,Parvez, Masood,Back, Thomas G.
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experimental part
p. 3508 - 3517
(2012/06/04)
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- Ammonium bromide as an effective and viable catalyst in the oxidation of sulfides using nitro urea and silica sulfuric acid
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A new catalytic method for the chemoselective oxidation of sulfides to the sulfoxides has been studied. A variety of dialkyl, alkylaryl and diaryl sulfides were subjected to the oxidation reaction by a mixture of nitro urea, derived from urea nitrate, silica sulfuric acid (SiO2-OSO3H) and catalytic amounts of ammonium bromide in CH2Cl2 at room temperature.
- Ghorbani-Choghamarani,Zamani
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experimental part
p. 142 - 148
(2012/01/03)
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- Trimethylphenylammonium tribromide as a new and efficient oxidizing agent for the oxidative coupling of thiols into disulfides and chemoselective oxidation of sulfides into sulfoxides
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Trimethylphenylammonium tribromide has been introduced as a versatile and new oxidizing agent for the preparation of disulfides and sulfoxides from thiols and sulfides, respectively. The reaction progress is simple, and proceeds under mild and homogenous conditions in ambient temperature. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor &Francis Group, LLC.
- Ghorbani-Choghamarani, Arash,Soleiman-Beigi, Mohammad,Noormohammadi, Farid
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scheme or table
p. 1665 - 1672
(2011/10/05)
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- Polyvinylpolypyrrolidone-supported hydrogen peroxide (PVP-H 2O2), silica sulfuric acid and catalytic amounts of ammonium bromide as green, mild and metal-free oxidizing media for the efficient oxidation of alcohols and sulfides
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Polyvinylpolypyrrolidone-supported hydrogen peroxide (PVP-H 2O2), silica sulfuric acid (SiO2OSO 3H) and catalytic amounts of ammonium bromide (NH4Br) are introduced as green media for the in situ generation of bromoniume ion (Br +), which was applied for the selective oxidation of sulfides and alcohols into sulfoxides and carbonyl compounds, respectively. The oxidation reactions were carried out heterogeneously in acetonitrile, as solvent, at room temperature (oxidation of sulfides) and/or 60 °C (oxidation of alcohols).
- Ghorbani-Choghamarani,Azadi
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experimental part
p. 1082 - 1090
(2012/02/15)
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- A recyclable fluorous thiourea organocatalyst for the chemoselective oxidation of sulfides
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As a kind of organocatalyst, 1-[4-(perfluorooctyl)phenyl]-3-phenylthiourea was employed to the chemoselective oxidation of sulfides in the presence of 30% H2O2. A variety of diaryl, dialkyl, alkyl aryl sulfides could be oxidized to s
- Huang, Yi-Bo,Yi, Wen-Bin,Cai, Chun
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experimental part
p. 554 - 557
(2011/08/22)
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- Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
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A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.
- Rioz-Martinez, Ana,Kopacz, Malgorzata,De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Gotor, Vicente,Fraaije, Marco W.
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experimental part
p. 1337 - 1341
(2011/04/23)
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- Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions
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An increasing number of reactions of sulfenic acid anions are being demonstrated in the literature. As such, mild, general and reliable means for the generation of sulfenates are due. In the current paper, an addition/elimination of 2-sulfinyl acrylates using various nucleophiles is demonstrated and evaluated as a protocol for alkane- and arenesulfenate generation. Cyclohexanethiolate, methoxide and n-butyllithum each exhibit some merit for the reaction, and the thiolate is established as a mild, selective and effective reagent to release sulfenates from 2-sulfinyl acrylates. The stereospecificity of the addition/elimination of each nucleophile is recognized, and an explanation for the specificity is offered for thiolate and methoxide.
- Singh, Suneel P.,O'Donnell, Jennifer S.,Schwan, Adrian L.
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supporting information; experimental part
p. 1712 - 1717
(2010/07/04)
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- Sulfoxidation with hydrogen peroxide catalyzed by [SeO 4{WO(O2)2}2]2-
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The selenium-containing dinuclear peroxotungstate, [(n-C4H 9)4N]2[SeO4{WO(O2) 2}2] (I), acts as a homogeneous catalyst for the selective oxidation of various kinds of cyclic mono- and disulfides with 30% aqueous H2O2. The cyclic disulfides were selectively oxidized to the corresponding monosulfoxides with one equivalent of H2O 2 with respect to the sulfides. In the presence of two equivalents of H2O2, the oxidation of dibenzothiophene gave the corresponding sulfone in 98% yield under the mild conditions. The negative Hammett ρ value (-0.62) for the competitive oxidation of p-substituted thioanisoles and the low XSO (XSO = (nucleophilic oxidation)/(total oxidation)) value of 0.14 for the I-catalyzed oxidation of thianthrene 5-oxide (SSO) revealed that I is a strong electrophilic oxidant. The reactivities of the di- and tetranuclear peroxotungstates with XO 4n- ligands (X = Se(vi), As(v), P(v), S(vi), and Si(iv)) were strongly dependent on the kinds of hetero atoms. The reaction rates for the sulfoxidation decreased with an increase in the XSO values and a peroxotungstate with a stronger electrophilicity was more active for the sulfoxidation. The kinetic and mechanistic investigations showed that the electrophilic attack of the peroxo oxygen at the sulfur atom is a key step in the sulfoxidation. The computational investigation supported the high chemoselectivitiy for the sulfoxidation of diallyl sulfide.
- Kamata, Keigo,Hirano, Tomohisa,Ishimoto, Ryo,Mizuno, Noritaka
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supporting information; experimental part
p. 5509 - 5518
(2010/08/04)
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- Tantalum carbide or niobium carbide catalyzed oxidation of sulfides with hydrogen peroxide: Highly efficient and chemoselective syntheses of sulfoxides and sulfones
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The oxidation of sulfides with 30% hydrogen peroxide catalyzed by tantalum carbide provided the corresponding sulfoxides in high yields. The reaction of sulfides with 30% hydrogen peroxide catalyzed by niobium carbide efficiently afforded the corresponding sulfones. These catalysts can easily be recovered from the reaction mixture and may be repeatedly used as catalysts for the oxidation without losing their activity. Georg Thieme Verlag Stuttgart New York.
- Kirihara, Masayuki,Itou, Atsushi,Noguchi, Takuya,Yamamoto, Junya
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experimental part
p. 1557 - 1561
(2010/09/05)
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- Catalytic oxidation of sulfides to sulfoxides by poly(4-vinyl pyridinium nitrate), silica sulfuric acid and ammonium bromide as a catalyst
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A new catalytic procedure for the chemoselective oxidation of sulfides to sulfoxides was studied. A variety of aliphatic and aromatic sulfides were subjected to sulfoxidation by combining poly(4-vinyl pyridinium nitrate), silica sulfuric acid (SiO2-OSO3H), and catalytic amounts of ammonium bromide in CH2Cl2 in the presence of a few drops of water at room temperature. Excellent yields were obtained.
- Ghorbani-Choghamarani, Arash,Sardari, Sara
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experimental part
p. 1347 - 1350
(2011/09/19)
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- CMPs as scaffolds for constructing porous catalytic frameworks: A built-in heterogeneous catalyst with high activity and selectivity based on nanoporous metalloporphyrin polymers
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This article describes the synthesis and functions of a porous catalytic framework based on conjugated micro- and mesoporous polymers with metalloporphyrin building blocks (FeP-CMP). FeP-CMP was newly synthesized via a Suzuki polycondensation reaction and was developed as a heterogeneous catalyst for the activation of molecular oxygen to convert sulfide to sulfoxide under ambient temperature and pressure. FeP-CMP is intriguing because the polymer skeleton itself is built from catalytic moieties and serves as built-in catalysts, bears inherent open nanometer-scale pores that are accessible for substrates, and possesses large surface areas (1270 m2 g -1) that facilitate the transformation reaction. It is highly efficient with high conversion (up to 99%) and a large turnover number (TON = 97,320), is widely applicable to various sulfides covering from aromatic to alkyl and cyclic substrates, displays high selectivity (up to 99%) to form corresponding sulfoxides, and is highly chemoselective for the oxidation of a sulfide group even in the coexistence of other oxidative functionalities. Owing to the covalent linkages between catalytic sites in the frameworks, FeP-CMP can be recycled with good retention of its porous structure and allows for large-scale transformation. These unique characteristics clearly originate from the covalent porous catalytic framework structure and demonstrate the usefulness of CMPs in the exploration of built-in heterogeneous catalysts, a new potential of these materials that have thus far been reported to exhibit noteworthy gas adsorption functions.
- Chen, Long,Yang, Yong,Jiang, Donglin
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supporting information; experimental part
p. 9138 - 9143
(2010/08/21)
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- SELECTIVE PRODUCTION OF SULPHOXIDES
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The invention pertains to a process for producing a sulphoxide compound, comprising oxidizing a thioether compound with an ozonide formed from a olefin and ozone, to obtain the corresponding sulphoxide compound, provided that the olefin is not ethene. The ozonide converts thio - ether compounds selectively, unlike its art - known oxidizing counterparts. The milder ozonide does not require manipulation of the stoichiometric amount of available oxidizing agent during the reaction, to prevent the formation of sulphones.
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