10154-72-0Relevant academic research and scientific papers
Generation of the Methoxycarbonyl Radical by Visible-Light Photoredox Catalysis and Its Conjugate Addition with Electron-Deficient Olefins
Slutskyy, Yuriy,Overman, Larry E.
, p. 2564 - 2567 (2016)
Visible-light photoredox-catalyzed fragmentation of methyl N-phthalimidoyl oxalate allows the direct construction of a 1,4-dicarbonyl structural motif by a conjugate addition of the methoxycarbonyl radical to reactive Michael acceptors. The regioselectivity of the addition of this alkoxyacyl radical species to electron-deficient olefins is heavily influenced by the electronic nature of the acceptor, behavior similar to that exhibited by nucleophilic alkyl radicals.
Multicomponent Synthesis of Sulfones and Sulfides from Triarylbismuthines and Sodium Metabisulfite in Deep Eutectic Solvents
Saavedra, Beatriz,Marset, Xavier,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 3462 - 3467 (2020/06/04)
This study describes a novel and catalyst-free methodology for the multicomponent synthesis of a broad range of sulfones, disulfides, and sulfides from non-toxic triarylbismuthines (Ar3Bi) and sodium metabisulfite (Na2S2O5) in deep eutectic solvents (DESs). The fine tuning of the DESs properties allowed the solubility of all reagents, enhancing their reactivity, as well as, the recyclability of the reaction medium for at least 5 consecutive cycles. Thus, this versatile strategy uses non-toxic reagents without the need of metal catalysts in a sustainable solvent, being an interesting alternative to traditional hazardous protocols.
Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant
Kupwade,Khot,Lad,Desai,Wadgaonkar
, p. 6875 - 6888 (2017/10/06)
Abstract: We describe here our journey from the failure of our attempts in controlled oxidation of sulfides to sulfoxides using an Oxone–KBr combination to our success in the development of a catalyst-free protocol for the oxidation of sulfides to sulfoxides using Oxone as an oxidant. We also describe the failure of our attempts at the oxidation of sulfides to sulfones using an excess of Oxone–KBr as well as Oxone, and our success towards the development of a rapid, scalable and chromatography-free protocol for the oxidation of sulfides to sulfones using diethylamine–Oxone as an unprecedented catalyst–oxidant combination.
Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C?S Bond Formation: Scope and Mechanistic Studies
Marset, Xavier,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 10522 - 10526 (2017/08/10)
A unique jigsaw catalytic system based on deep eutectic solvents and palladium nanoparticles where C?S bonds are formed from aryl boronic acids and sodium metabisulfite, is introduced. The functionalization step is compatible with a broad spectrum of reagents such as nucleophiles, electrophiles or radical scavengers. This versatile approach allows the formation of different types of products in an environmentally friendly medium by selecting the components of the reaction, which engage one with another as pieces in a jigsaw. This simple procedure avoids the use of toxic volatile organic solvents allowing the formation of complex molecules in a one-pot reaction under mild conditions. Despite the fact that only 1 mol % of metal loading is used, the recyclability of the catalytic system is possible. Kinetic experiments were performed and the reaction order for all reagents, catalyst and ligand was determined. The obtained results were compared to palladium nanocrystals of different known shapes in order to shed some light on the properties of the catalyst.
Synthesis of alkyl aryl sulfones via reaction of N-arylsulfonyl hydroxyamines with electron-deficient alkenes
Bin, Yunhui,Hua, Ruimao
, (2017/01/24)
Alkyl aryl sulfones were prepared in high yields via the reaction of N-arylsulfonyl hydroxylamines with electron-deficient alkenes. These reactions have the advantages of simplicity, easily available starting materials and mild reaction conditions.
Method for preparing substituted ethyl aryl sulfone
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Paragraph 0044-0045, (2017/03/23)
The invention discloses a method for preparing substituted ethyl aryl sulfone. The method comprises the following steps: a compound shown in a formula II, a compound shown in a formula III and alkali are uniformly mixed in a solvent and are subjected to a coupling reaction, a compound shown in a formula I containing R2' as -CH2CH2R is obtained after the reaction is complete; or the method comprises the following steps: the compound shown in the formula II, ethyl propiolate and alkali are uniformly mixed in the solvent and then are subjected to the coupling reaction, and the compound shown in a formula I containing R2' as -CH=CH2=OOCH2CH3 is obtained after the reaction is complete. The method has the advantages of universality, convenience, simple reaction system, and mild reaction condition; the reaction can be amplified to a gram level, the reaction raw materials are simple and easily available, the used alkali and raw materials have the advantages of low cost and easy acquisition, the atom utilization rate is high, and solvent toxicity is low.
Addition of sulfinic acids to methacrylic derivatives
Ivanova,Aleksiev
experimental part, p. 38 - 43 (2011/03/22)
The kinetics of the addition of arenesulfinic acids to methacrylic derivatives were studied. The reactions were found to be second order over a range of concentrations from 0.01 to 0.10 M. For pH values ranging from 4 to 8, the following rate constants were obtained pH the methylacrylate, chloromethylacrylate, and bromomethylacrylate with benzenesulfinic acids (278 K) were investigated: 2.37 (± 0.2).10-4 M-1s -1, 2.60 (± 0.1).10-4 M-1s-1, 3.15 (± 0.3).10-4 M-1s-1. Copyright Taylor & Francis Group, LLC.
Chemoselective sulfoxidation by H2O2 or HNO3 using a phosphate impregnated titania catalyst
Bharadwaj, Saitanya K.,Sharma, Susanda N.,Hussain, Sahid,Chaudhuri, Mihir K.
experimental part, p. 3767 - 3771 (2009/10/11)
A variety of organosulfur compounds have been selectively oxidized to the corresponding sulfoxides by either H2O2 or HNO3 using a newly developed solid acid catalyst composed of 84.5% of TiO2 and 15.5% of [Ti4H11(PO4)9]·nH2O (n = 1-4). The chemoselective oxidation of sulfides in the presence of vulnerable groups such as -CN, -C{double bond, long}C-, -CHO, or -OH, as well as sulfoxidation of substrates like benzothiazole, glycosyl sulfide, and dibenzothiophenes is some of the important attribute of the protocol. Nitric acid, under the present experimental conditions, brings about relatively better selectivity than hydrogen peroxide.
Borax-catalyzed and pH-Controlled selective oxidation of organic sulfides by H2O2: An environmentally clean protocol
Hussain, Sahid,Bharadwaj, Saitanya K.,Pandey, Ravindra,Chaudhuri, Mihir K.
experimental part, p. 3319 - 3322 (2011/03/17)
The selective oxidation of sulfides to sulfoxides and sulfones was achieved in high yields at: room temperature with borax as a recyclable catalyst and H2O2 as the terminal oxidant by varying the pH of the reaction medium. The borax/H2O2 system can chemoselectively oxidize alkyl and aryl sulfides in the presence of oxidation-prone functional, groups such as C=C, -CN, and -OH.
Tin-free, radical-mediated γ-alkylations of α,β- unsaturated esters via O-tert-alkyl dienol ethers
Jin, Young Lee,Kim, Sunggak
, p. 49 - 54 (2008/09/21)
Tin-free, radical-mediated γ-alkylation of α,β-unsaturated esters is accomplished by radical addition and β-fragmentation of O-tert-alkyl dienol ethers and subsequent iodine atom transfer process. Georg Thieme Verlag Stuttgart.
