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Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Fiorio, Jhonatan L.,Rossi, Liane M.
p. 312 - 318
(2021/01/29)

N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides
An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.
Wang, Jianqiang,Shi, Fangmin,Dai, Dongyan,Xiong, Liping,Yang, Yongpo
supporting information
p. 439 - 443
(2021/02/03)

Scalable electrochemical reduction of sulfoxides to sulfides
A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.
Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi
supporting information
p. 2773 - 2777
(2021/04/21)

Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols
This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.
Mitamura, Kanju,Yatabe, Takafumi,Yamamoto, Kidai,Yabe, Tomohiro,Suzuki, Kosuke,Yamaguchi, Kazuya
supporting information
p. 3749 - 3752
(2021/04/21)

Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions
In this work, the immobilization of copper(ii) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfidesviathe reaction of aryl halides with thiourea as the sulfur source in the presence of NaOH instead of former strongly basic and harsh reaction conditions. Under optimum conditions, the synthesis yields of sulfoxides, symmetrical sulfides, and disulfides were about 99%, 95%, and 96% respectively with highest selectivity. The heterogeneous copper-based catalyst has advantages such as the easy recyclability of the catalyst, the easy separation of the product and the less wastage of products during the separation of the catalyst. This heterogeneous nanocatalyst was characterized by FESEM, FT-IR, VSM, XRD, EDX, ICP and TGA. Furthermore, the recycled catalyst can be reused for several runs and is economically effective.
Yarmohammadi, Nasrin,Ghadermazi, Mohammad,Mozafari, Roya
p. 9366 - 9380
(2021/03/16)

Methods, Syntheses and Characterization of Diaryl, Aryl Benzyl, and Dibenzyl Sulfides
Twenty-four aryl benzyl sulfides, diaryl sulfides and dibenzyl sulfides were synthesized by four methods and characterized by 1H NMR, FT-IR and Gas chromatography. The reaction conditions of different synthesis methods were studied from the aspects of time, solvent, base and dispersant. The molecular structures of benzylphenyl sulfide (2S), (4-tert-butylbenzyl)(4-methylphenyl) sulfide (4S), (4-methylbenzyl)(4-methylphenyl) sulfide (9S), di(4-methylphenyl) sulfide (11S), (3,5-dimethylphenyl)(4-methyl phenyl) sulfide (15S), and dibenzyl sulfide (19S) [22] have been determined by single-crystal X-ray crystallography. Compounds 2S and 15S crystallize in the monoclinic space group P21/c, with a = 12.278(3), b = 15.894(3), c = 5.6056(11) ?, β = 94.532(2)°, and Z = 4 for 2S, and a = 9.800(9), b = 7.950(7), c = 16.690(15) ?, β = 100.890(12)°, and Z = 4 for 15S. The unit cell of 4S has a triclinic Pī symmetry with the cell parameters a = 6.0436(10), b = 8.7871(14), c = 15.535(2) ?, α = 81.921(2)°, β = 81.977(2)°, γ = 80.889(2)°, and Z = 2. Compounds 9S and 11S both crystallize in the orthorhombic space group P212121, with a = 6.188(3), b = 8.041(4), c = 26.005(14) ?, and Z = 4 for 9S, and a = 5.835(2), b = 8.010(3), c = 25.131(9) ?, and Z = 4 for 11S. Graphic Abstract: Twenty-four aryl sulfide compounds with different substituents were synthesized and characterized, and the molecular structures of six different sulfide compounds have been determined by single-crystal X-ray crystallography.[Figure not available: see fulltext.]
Zhou, Wen-Yan,Chen, Min,Zhang, Pei-Zhi,Jia, Ai-Quan,Zhang, Qian-Feng
p. 301 - 310
(2020/09/07)

Oxygen-to-Oxygen Silyl Migration of α-Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation
Oxidation of α-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C-S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was used to develop oxidation-triggered allicin donors.
Kelly, Shane S.,Shen, Tun-Li,Xian, Ming
supporting information
p. 3741 - 3745
(2021/05/10)

One-Pot Synthesis of Thiocarbamates
An efficient isocyanide-based synthesis of S-thiocarbamates was discovered and thoroughly investigated. The new reaction protocol is a one-pot procedure and allows the direct conversion of N-formamides into thiocarbamates by initial dehydration with p-toluene sulfonyl chloride to the respective isocyanide and subsequent addition of a sulfoxide component. Contrary to recent literature, which also uses isocyanides as starting material, but with other sulfur reagents than sulfoxides, in this protocol, no isolation and purification of the isocyanide component is necessary, thus significantly decreasing the environmental impact and increasing the efficiency of the synthesis. The new protocol was applied to synthesize a library of sixteen thiocarbamates, applying four N-formamides and four commercially available sulfoxides. Furthermore, experiments were conducted to investigate the reaction mechanism. Finally, four norbornene-based thiocarbamate monomers were prepared and applied in controlled ring-opening metathesis polymerization (ROMP) reactions. The polymers were characterized by size-exclusion chromatography (SEC) and their properties were investigated utilizing differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).
Barther, Dennis,Malliaridou, Triantafillia,Meier, Michael A. R.,Moatsou, Dafni,Waibel, Kevin A.
supporting information
p. 4508 - 4516
(2021/08/30)

Catalytic dehydrogenation of amines to imines and the in-situ reduction of sulfoxides into sulfides
The catalytic acceptorless dehydrogenation of primary amines into imines and H2 represents one of the most important organic transformations, and the in-situ utilization of the generated H2 for chemical reduction reactions has never
Li, Bo,Liu, Bing,Liu, Xixi,Wang, Wei,Wang, Yanxin,Xiang, Nian,Zhang, Zehui
p. 81 - 88
(2021/07/30)

Photocatalytic synthesis method of aryl thioether and derivatives thereof
The invention belongs to the field of organic synthesis, and particularly relates to a photocatalytic synthesis method of aryl thioether and derivatives thereof. The synthesis method comprises the steps: dissolving an N-(sulfanyl) amide compound into a methyl aromatic compound under the protection of inert gas, and thus obtaining the aryl thioether compound under the action of light, a catalyst, aligand and alkali. According to the method, the coupling reaction of a C-S bond is completed through visible light induction by utilizing a light/Ni dual-catalytic system, so that the method has goodfunctional group compatibility, and the C-S bond compound can be selectively and efficiently constructed in one step. The method has the advantages of simple catalytic system, mild reaction conditions, economical, simple and easily available substrate, simple reaction operation and the like.
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(2021/04/03)

Synthesis method of dibenzyl sulfide
As an important organic intermediate and a synthesis reagent, an organic sulfur compound also has unique pharmacological effects of resisting tumors, inflammation, bacteria and oxidation, preventing aging, preventing and treating cardiovascular diseases and the like. The patent develops a method for synthesizing dibenzyl sulfide without metal catalysis. In an acetonitrile solution, benzyl trifluoromethanesulfonic acid quaternary ammonium salt and sodium sulfide nonahydrate are used to synthesize dibenzyl sulfide in a wide substrate range with good to excellent yield through breakage of a carbon-nitrogen bond and generation of a carbon-sulfur bond. The method has the advantages of mild reaction conditions, simple operation, no metal, high yield, wide substrate applicability and the like.
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Paragraph 0008-0012

(2021/02/06)

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications
The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.
Clarke, Aimee K.,Parkin, Alison,Rossi-Ashton, James A.,Taylor, Richard J. K.,Unsworth, William P.
p. 5814 - 5820
(2020/07/21)

B2cat2-Mediated Reduction of Sulfoxides to Sulfides
An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.
Takahashi, Fumiya,Nogi, Keisuke,Yorimitsu, Hideki
supporting information
p. 3009 - 3012
(2020/03/25)

Photochemical Functionalization of Heterocycles with EBX Reagents: C?H Alkynylation versus Deconstructive Ring Cleavage**
The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C?H functionalization of saturated O-heterocycles, as well as the deconstructive ring-cleavage of S-heterocycles, employing hypervalent iodine alkynylation reagents (ethynylbenziodoxolones, EBX). This photochemical alkynylation is performed utilizing phenylglyoxylic acid as the photoinitiator, leading to the corresponding products in good to high yields, under household fluorescent light bulb irradiation. When O-heterocycles were employed, the expected α-C?H alkynylation took place. In contrast, oxidative ring-opening to form a thioalkyne and an aldehyde was observed with S-heterocycles. Preliminary mechanistic experiments are presented to give first insights into this puzzling divergent reactivity.
Voutyritsa, Errika,Garreau, Marion,Kokotou, Maroula G.,Triandafillidi, Ierasia,Waser, Jér?me,Kokotos, Christoforos G.
supporting information
p. 14453 - 14460
(2020/10/12)

Phosphonate Decomposition-Induced Polyoxomolybdate Dumbbell-Type Cluster Formation: Structural Analysis, Proton Conduction, and Catalytic Sulfoxide Reduction
The reaction of MoO42- with a number of phosphonic acids [bis(phosphonomethyl)glycine, R,S-hydroxyphosphonoacetic acid, 1-hydroxyethane-1,1-diphosphonic acid, phenylphosphonic acid, aminotris(methylene phosphonic acid), and 1,2-ethylenediphosphonic acid] under oxidizing (H2O2) hydrothermal conditions at low pH leads to rupture of the P-C bond, release of orthophosphate ions, and generation of the octanuclear, phosphate-bridged, polyoxometalate molybdenum cluster (NH4)5[Mo8(OH)2O24(μ8-PO4)](H2O)2 (POMPhos). This cluster has been fully characterized and its structure determined. It was studied as a proton conductor, giving moderate values of σ = 2.13 × 10-5 S·cm-1 (25 °C) and 1.17 × 10-4 S·cm-1 (80 °C) at 95% relative humidity, with Ea = 0.27 eV. The POMPhos cluster was then thermally treated at 310 °C, yielding (NH4)2.6(H3O)0.4(PO4Mo12O36) together with an amorphous impurity containing phosphate and molybdenum oxide. This product was also studied for its proton conductivity properties, giving rise to an impressively high value of σ = 2.43 × 10-3 S·cm-1 (25 °C) and 6.67 × 10-3 S·cm-1 (80 °C) at 95% relative humidity, 2 orders of magnitude higher than those corresponding to the "as-synthesized" solid. The utilization of POMPhos in catalytic reduction of different sulfoxides was also evaluated. POMPhos acts as an efficient homogeneous catalyst for the reduction of diphenyl sulfoxide to diphenyl sulfide, as a model reaction. Pinacol was used as a low-cost, environmentally friendly, and highly efficient reducing agent. The effects of different reaction parameters were investigated, namely the type of solvent and reducing agent, presence of acid promoter, reaction time and temperature, loading of catalyst and pinacol, allowing to achieve up to 84-99% yields of sulfide products under optimized conditions. Substrate scope was tested on the examples of diaryl, alkylaryl, dibenzyl, and dialkyl sulfoxides and excellent product yields were obtained.
Armakola, Eirini,Salcedo, Inés R.,Bazaga-García, Montse,Olivera-Pastor, Pascual,Mezei, Gellert,Cabeza, Aurelio,Fernandes, Tiago A.,Kirillov, Alexander M.,Demadis, Konstantinos D.
supporting information
p. 11522 - 11533
(2019/09/03)

A Manganese N-Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes
The first reduction of sulfoxides catalysed by a well-defined manganese complex is described. A variety of sulfoxides are reduced to the corresponding sulfides in high yields using phenylsilane, diphenylsilane, and the economically feasible 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agents in the presence of a Mn-NHC complex. The reaction is performed under air and without the need of any additive. The involvement of radicals in the catalytic reaction is probed by spin-trap experiments.
Sousa, Sara C. A.,Carrasco, Carlos J.,Pinto, Mara F.,Royo, Beatriz
p. 3839 - 3843
(2019/06/24)

Synthesis method of thioether compounds
The invention discloses a synthesis method of thioether compounds. The method comprises steps as follows: phosphorus trichloride and a solvent with uniformly distributed sulfoxide compounds are mixeduniformly, after mixing, the mixture is subjected to a reaction at the temperature of 20-25 DEG C for 0.5-6 h, and the thioether compounds are obtained, wherein the solvent is acetonitrile. Compared with the prior art, the synthesis method has the advantages that raw materials are cheap and easy to obtain, a reducer is cheap and easy to obtain and store, and a series of thioether compounds can beobtained.
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(2019/08/02)

Core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C) as a highly efficient and recoverable nanocatalyst for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides
Fe3O4 magnetic nanoparticles were used as a core for Cu(II) Schiff base complex functionalized mesoporous MCM-41 shell to provide a core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C). A simple, environmentally friendly, inexpensive, green reaction conditions and efficient procedure for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides derivatives using this core–shell nanostructure as an efficient, novel and recoverable nanocatalyst has been described. Fe3O4?MCM-41?Cu-P2C is stable, cost-effective, heterogeneous, easy to handle and recoverable nanocatalyst and can be reused for several consecutive runs without a significant loss of catalytic activity. The catalyst was characterized by fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), powder X-ray diffractometer (XRD), scanning electron microscopy (SEM), atomic absorption spectroscopy (AAS), Brunauer–Emmett–Teller (BET) and vibrating sample magnetometer (VSM) techniques.
Nikoorazm, Mohsen,Erfani, Zahra
(2019/10/11)

Immobilization of Pd(0) complex on the surface of SBA-15: A reusable catalyst for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides
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
p. 374 - 380
(2018/11/01)

Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols
Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.
Corma, Avelino,Sorribes, Iván
p. 3130 - 3142
(2019/03/13)

Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol
It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.
Ma, Xiantao,Yu, Jing,Yan, Ran,Yan, Mengli,Xu, Qing
p. 11294 - 11300
(2019/09/12)

Preparation and Characterization of Ni-Modified Graphene Oxide Complex as an Efficient Catalyst for the Synthesis of Sulfides via Reaction of Arylhalides with S8 or Thiourea
In this work, complex of Ni-modified graphene oxide was prepared and characterized using FT-IR spectroscopy, SEM, XRD, TGA and ICP-OES techniques. This compound used as an efficient and recoverable catalyst for the C–S coupling reaction using sulfur-transfer reagents (S8 or thiourea). The catalyst was easily separated using a simple filtration and reusable without significant loss of their catalytic efficiency.
Ghafouri-Nejad, Raziyeh,Hajjami, Maryam,Nejat, Razieh
(2018/01/27)

Deoxygenation of sulphoxides to sulphides with trichlorophosphane
An efficient route to deoxygenation of sulphoxides to sulphides with PCl3 under mild reaction condition was developed. PCl3 was used as a reducing agent for the first time to convert sulphoxides to sulphides. The mild conditions, use of cheap and readily available reagent, and broad substrate scope render it a useful strategy for preparing sulphides.
Zhao, Xia,Zheng, Xiancai,Yang, Bo,Sheng, Jianqiao,Lu, Kui
p. 1200 - 1204
(2018/02/21)

Application of Silicon-Initiated Water Splitting for the Reduction of Organic Substrates
The use of water as a donor for hydrogen suitable for the reduction of several important classes of organic compounds is described. It is found that the reductive water splitting can be promoted by several metalloids among which silicon shows the best efficiency. The developed methodologies were applied for the reduction of nitro compounds, N-oxides, sulfoxides, alkenes, alkynes, hydrodehalogenation as well as for the gram-scale synthesis of several substrates of industrial importance.
Gevorgyan, Ashot,Mkrtchyan, Satenik,Grigoryan, Tatevik,Iaroshenko, Viktor O.
p. 375 - 382
(2018/06/04)

Supported Rhodium Nanoparticles Catalyzed Reduction of Nitroarenes, Arylcarbonyls and Aryl/Benzyl Sulfoxides using Ethanol/Methanol as In Situ Hydrogen Source
A facile reduction reaction of nitroarenes, aryl carbonyls and aryl/benzyl sulfoxides was performed under polystyrene supported rhodium (Rh@PS) catalyzed conditions using ethanol/methanol as in situ hydrogen source. The catalyst Rh@PS played a pivotal role in the oxidation of ethanol/methanol in the presence of traces of aerial oxygen and base to produce hydrogen gas, enough for further reduction reaction. Transmission electron microscopy (TEM) analysis indicated that the average particle size of the Rh nanoparticles (NPs) lies between 2–3 nm; this is responsible for its high catalytic activity. The advantages of Rh@PS are its catalytic activity, easy preparation, recovery, recyclability for several runs, and low metal leaching during reaction. (Figure presented.).
Sharma, Saurabh,Bhattacherjee, Dhananjay,Das, Pralay
supporting information
p. 2131 - 2137
(2018/04/17)

Cu (II) and Cd (II) anchored functionalized mesoporous SBA-15 as novel, highly efficient and recoverable heterogeneous catalysts for green oxidative coupling of thiols and C–S cross-coupling reaction of aryl halides
Two novel heterogeneous catalysts have been synthesized by anchoring Cu and Cd Creatinine complexes onto the surface of mesochannels of SBA-15 for highly efficient oxidative coupling of thiols to disulfides using hydrogen peroxide and synthesis of sulfides using S8 and KOH. The structure of the prepared catalysts was determined using SEM, FT-IR, X-ray diffraction, elemental analysis, N2 adsorption–desorption analysis and TGA. The catalysts significantly enhanced the reaction rate of the oxidative coupling of thiols and C–S bond formations. The catalysts were reused several times without appreciable loss in their activity.
Molaei, Somayeh,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
p. 35 - 47
(2018/10/02)

Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-one, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41
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
p. 857 - 872
(2018/03/01)

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
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
(2018/03/21)

Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides
A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.
Liu, Ting,Qiu, Renhua,Zhu, Longzhi,Yin, Shuang-Feng,Au, Chak-Tong,Kambe, Nobuaki
supporting information
p. 3833 - 3837
(2018/12/05)

A photoredox catalyzed iminyl radical-triggered C-C bond cleavage/addition/Kornblum oxidation cascade of oxime esters and styrenes: synthesis of ketonitriles
A photoredox-catalyzed iminyl radical-triggered C-C bond cleavage/addition/Kornblum oxidation cascade of cycloketone oxime esters and styrenes in DMSO is described. This three-component, one-pot procedure features mild conditions, a broad substrate scope, and high functional group tolerance, providing an efficient approach to access diversely functionalized ketonitriles.
He, Bin-Qing,Yu, Xiao-Ye,Wang, Peng-Zi,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information
p. 12262 - 12265
(2018/11/21)

TfNHNHBoc as a SCF3 source for the sulfenylation of indoles
An unprecedented use of trifluoromethanesulfonyl hydrazides as effective SCF3 sources has been established in the sulfenylation of indoles. A range of substituted indoles participated in CuCl-catalyzed oxidative sulfenylation reaction with TfNHNHBoc in the presence of dimethyl sulfoxide to furnish structurally diverse 3-indolyl trifluoromethyl thioethers in moderate to good yields with very high regioselectivity.
Guo, Jing-Yu,Dai, Rui-Han,Xu, Wen-Cong,Wu, Ruo-Xin,Tian, Shi-Kai
supporting information
p. 8980 - 8982
(2018/08/21)

Indium-catalyzed direct conversion of dibenzyl ethers to dibenzyl sulfides using elemental sulfur and a hydrosilane and its application to the preparation of benzyl selenides
Described herein is a catalytic system composed of an indium(III) compound, a hydrosilane and an easily handled form of elemental sulfur (S8) that effectively and directly catalyzes the sulfidation of dibenzyl ethers to produce dibenzyl sulfides. This system could also be applied to selenium in a straightforward conversion to dibenzyl selenides.
Sakai, Norio,Takada, Koji,Katayama, Masahiro,Ogiwara, Yohei
p. 791 - 793
(2018/06/12)

An efficient and recyclable catalytic system for carbon–sulfur coupling reaction and synthesis of 5-substituted 1H-tetrazoles
In this research paper, efficient and economical protocols for the synthesis of symmetrical sulfides and 5-substituted 1H-tetrazoles have been reported using Fe3O4@SBTU@Ni(II) as a heterogeneous and recoverable nanocatalyst. The noticeable features of this catalytic system are: operational simplicity, environmentally benign, easier work-up procedure, green and efficient synthetic entry to excellent yield of products in a high reusability and applicability to various starting materials and, therefore, cost efficiency.
Ghorbani-Choghamarani, Arash,Moradi, Zahra,Azadi, Gouhar
p. 237 - 251
(2018/01/04)

Efficient Generation of C–S Bonds via a By-Product-Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea
A metal- and base-free three-component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially-active thioethers. Mechanistic studies revealed that a by-product-promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction. (Figure presented.).
Ma, Xiantao,Yu, Lei,Su, Chenliang,Yang, Yaqi,Li, Huan,Xu, Qing
supporting information
p. 1649 - 1655
(2017/05/29)

Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst
The general reduction of phosphine oxides, sulfoxides, and amine N-oxides was achieved by combining bis(2-chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2-chlorophenyl)borinic acid as a precatalyst.
Chardon, Aurélien,Maubert, Orianne,Rouden, Jacques,Blanchet, Jér?me
p. 4460 - 4464
(2017/11/22)

Rapid and efficient deoxygenation of sulfoxides to sulfides with tantalum(V) chloride/sodium iodide system
TaCl5/NaI system converts a wide range of sulfoxides to the corresponding sulfides in high yields with short reaction times, under mild conditions. It is worth mentioning that this protocol is chemoselective and tolerates various functional groups (such as –Br, –Cl, –OCH3, –CHO, and –NO2) and double bond.
Yoo, Byung Woo,Park, Jeeyeon,Shin, Hyo Jong,Yoon, Cheol Min
p. 597 - 603
(2017/10/06)

B(C 6 F 5) 3 -Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes
B(C 6 F 5) 3 is shown to catalyze the deoxygenation of sulfoxides and sulfones to the corresponding sulfides with Et 3 SiH as the stoichiometric hydride source. While the method is limited in terms of functional group tolerance, it is applicable to the reduction of alkyl/aryl-, aryl/aryl-, and alkyl/alkyl-substituted sulfoxides, including the benzyl/benzyl-substituted derivative. The same protocol converts alkyl/aryl- but not aryl/aryl-substituted sulfones into sulfides.
Porwal, Digvijay,Oestreich, Martin
p. 4698 - 4702
(2017/10/05)

Reactions of Sulfur-Containing Organic Compounds and Peptides in 1-Ethyl-3-methyl-imidazolium Acetate
The neat ionic liquid (IL) [C2mim][OAc] is not just capable of dissolving thiol- and disulfide-containing compounds, but is able to chemically react with them without addition of any catalytic reagent. Through the analysis of four small organic molecules and a cysteine-containing peptide we could postulate a general reaction mechanism. Here, the imidazolium-carbenes preferentially react with the disulfide bond, but not thiol group. Moreover, the imidazole moiety was found to abstract the sulfur atom from the cysteine residue, providing an alternative way to transform Cys residues, which were artificially inserted into a peptide sequence in order to perform native chemical ligation (NCL) of two peptide fragments. Finally, the chemical reaction of [C2mim][OAc] with a cysteine-containing biomolecules can be tuned or even suppressed through the addition of at least 30% of water to the reaction mixture.
Baumruck, Andreas C.,Tietze, Daniel,Stark, Annegret,Tietze, Alesia A.
p. 7538 - 7545
(2017/07/26)

Anchoring of Cu(II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides
A copper(II)–vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H2O2 as a green oxidant and in the synthesis of 5-substituted 1H–tetrazoles from a smooth (3?+?2) cycloaddition of organic nitriles with sodium azide (NaN3). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.
Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
(2017/09/01)

Synthesis of sulfides via reaction of aryl/alkyl halides with S8 as a sulfur-transfer reagent catalyzed by Fe3O4-magnetic-nanoparticles-supported L-Histidine-Ni(II)
One-pot synthesis of symmetrical diaryl/alkyl sulfides in high yields from the reaction between aryl/alkyl halides and S8 can be carried out in a short period, using Fe3O4@SiO2@His@Ni(II) as a reusable catalyst. The present approach offers the advantages of a clean reaction, simple methodology and high efficiency, and avoids the use of a toxic catalyst.
Azadi, Gouhar,Taherinia, Zahra,Naghipour, Ali,Ghorbani-Choghamarani, Arash
p. 303 - 313
(2017/05/04)

The first report on the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles applied as versatile catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides
We have reported the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles for the first time as a novel, non-toxic, inexpensive and recyclable catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides (via reaction of aryl halides with S8 or 2-thiobarbituric acid as sulfur transfer reagents). The structure of the catalyst was studied by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), atomic absorption spectroscopy (AAS), UV-visible absorption and fluorescence spectroscopy.
Ghorbani-Choghamarani, Arash,Taherinia, Zahra
p. 9414 - 9423
(2017/08/29)

Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides
Alcohols can be efficiently converted into the useful thioethers by a transition metal- and base-free dehydrative S-alkylation reaction with thiols or disulfides by employing alkyl halides as the effective catalyst. This simple and efficient method is a green and practical way for the preparation of thioethers, as it tolerates a wide range of substrates such as aryl and alkyl thiols, as well as benzylic, allylic, secondary, tertiary, and even the less reactive aliphatic alcohols.
Yang, Yaqi,Ye, Zihang,Zhang, Xu,Zhou, Yipeng,Ma, Xiantao,Cao, Hongen,Li, Huan,Yu, Lei,Xu, Qing
supporting information
p. 9638 - 9642
(2017/11/30)

Electrochemical synthesis of organochalcogenides in aqueous medium
The electrochemical preparation of telluride, selenide and sulfide ions was carried out in NaOH aqueous solution, using a two compartment cell. Organochalcogenides were prepared from halogenated compounds in a two-step procedure. The monochalcogenides were obtained as the major products in good yields.
Ribeiro Neto, Pedro B.,Santana, Sonydelane O.,Levitre, Guillaume,Galdino, Danilo,Oliveira, Jadson L.,Ribeiro, Rogério T.,Barros, Maria E. S. B.,Bieber, Lothar W.,Menezes, Paulo H.,Navarro, Marcelo
supporting information
p. 657 - 661
(2016/02/12)

A method of preparing dibenzyl sulfide product
The invention discloses a method of preparing a benzyl disulfide product, and belongs to the technical field of a polymer antioxidant and a medicine intermediate. The method comprises the following steps of: adding benzyl chloride, triethylamine, an organic solvent and a phase transfer catalyst into a sealed reaction kettle according to a proportion, carrying out nitrogen gas displacement and adding hydrogen sulfide; stirring and heating to 50 DEG C-80 DEG C, and preserving heat for reacting for 2 hours-5 hours, wherein reaction mixed liquor obtained after the reaction is ended is a solid-liquid mixture; cooling to 25 DEG C-28 DEG C, filtering, washing a filter cake triethylamine hydrochloride by an organic solvent, combining washing liquid with filtrate, distilling, evaporating part of the organic solvent, cooling to 2 DEG C-7 DEG C to crystallize and separate out a product, washing by alcohol aqueous liquor, and drying to obtain the benzyl disulfide product which is a white crystal in outline. The product obtained by the technical process is high in yield and good in quality, and low in production cost; a reaction system is in an anhydrous system, so that sewage discharge is effectively avoided, and therefore, the method is convenient for realizing industrial production.
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Paragraph 0025; 0026

(2017/06/20)

Phase-vanishing method with gas evolution and its application to organic synthesis
Using a phase-vanishing (PV) system, hydrogen, oxygen, and hydrogen sulfide generated in situ from CaH2, KO2, and P2S5, respectively, were directly reacted with substances in the organic phase to afford the desired products. The selective synthesis of sulfides and disulfides was achieved with the evolution of H2S gas via tuning the bases used in the PV method. Using this PV system, reactions with hazardous gaseous reagents can be carried out easily and safely in a common test tube.
Matake, Ryosuke,Niwa, Yuki,Matsubara, Hiroshi
p. 672 - 675
(2016/01/26)

Hydrodeoxygenation of sulfoxides to sulfides by a Pt and MoOx co-loaded TiO2 catalyst
Supported metal nanoparticle catalysts were studied for the hydrodeoxygenation of sulfoxides to sulfides under solvent-free and mild conditions (50-155 °C, 1 or 7 atm H2). The catalytic activity for the model reaction of diphenyl sulfoxide depended on the type of metals, support materials and co-loaded oxides of transition metals (V, Nb, Mo, W, Re). Pt and MoOx co-loaded TiO2 (Pt-MoOx/TiO2) showed the highest activity. Pt-MoOx/TiO2 was reusable after the reaction and was effective for the reduction of various sulfoxides and showed a higher turnover number (TON) than previously reported catalysts. Using Pt-MoOx/TiO2, benzylphenylsulfone was reduced by H2 to give phenylbenzyl sulfide via benzylphenyl sulfoxides, which represented the first example of catalytic conversion of a sulfone to a sulfide by H2. Characterization studies of Pt-MoOx/TiO2 show that the surface of TiO2 is covered by small (or thin layer) Mo oxide species with exposed Mo cations as Lewis acid sites, and 4-5 nm sized Pt metal nanoparticles are supported on the Mo oxide-covered TiO2.
Touchy, Abeda Sultana,Hakim Siddiki,Onodera, Wataru,Kon, Kenichi,Shimizu, Ken-Ichi
p. 2554 - 2560
(2016/05/19)

A mild, efficient, and selective procedure for the deoxygenation of sulfoxides with the TaCl5/indium system
The TaCl5/In systemwas found to be a new reagent for reducing a wide range of structurally diverse sulfoxides to the corresponding sulfides with high yields under mild conditions. This protocol is chemoselective and tolerates several functional groups, such as Br, Cl, OCH3, CHO, and CH= CH2.
Yoo, Byung Woo,Lee, Min Kyung,Yoon, Cheol Min
p. 807 - 810
(2016/07/06)

Synthesis of Thioethers Using Triethylamine-Activated Phosphorus Decasulfide (P410
The synthesis of thioethers in excellent yields was achieved under mild conditions via the displacement reaction of halogens by sulfur. The cross-reaction of 2-(α-bromoacetyl)thiophene with triethylamine-activated phosphorus decasulfide (Et3N-P2S5) was elaborated by utilizing DFT calculations.
Turkoglu, Gulsen,Cinar, M. Emin,Ozturk, Turan
p. 3618 - 3624
(2016/10/17)

Synthesis of peptide nanofibers decorated with palladium nanoparticles and its application as an efficient catalyst for the synthesis of sulfides: Via reaction of aryl halides with thiourea or 2-mercaptobenzothiazole
In this work supported Pd nanoparticles on a peptide nanofiber (PdNP-PNF) have been prepared via fabrication of self-assembled woven nanofiber from peptide, subsequently immobilization of palladium nanoparticles on this nanostructural compound. To obtain self-assembled woven nanofiber, we designed and synthesized a peptide using arginine as building block. The C-terminus of amino acid was protected as ethylester. Coupling was mediated by dicyclohexylecarbodiimide-1-hydroxybenzotriazole (DCC-HOBT). TEM, SEM, XRD, ICP and FT-IR techniques were employed to characterize prepared nanofiber materials. In this work, the effect of phosphate buffer solutions pH 8 and pH 11 (isoelectric point of arginine amino acid) on the structure of peptide nanofiber was investigated. Supported Pd nanoparticles on the peptide nanofiber (PdNP-PNF) were applied for the C-S coupling reaction using two different sulfur transfer reagents (thiourea and 2-mercaptobenzothiazole).
Ghorbani-Choghamarani, Arash,Taherinia, Zahra
p. 59410 - 59421
(2016/07/06)

Indium-catalyzed direct preparation of dibenzyl sulfides from benzyl alcohols and elemental sulfur with a hydrosilane and its application to the preparation of dibenzyl selenide
We describe how a reducing system composed of InI3 and a hydrosilane efficiently and directly introduce elemental sulfur into the structure of dibenzyl sulfides via a nucleophilic substitution of benzyl alcohols. Also, we describe the application of this reducing system in the direct preparation of a dibenzyl selenide derivative with selenium.
Miyazaki, Takahiro,Katayama, Masahiro,Yoshimoto, Shunsuke,Ogiwara, Yohei,Sakai, Norio
supporting information
p. 676 - 679
(2016/01/26)