cas 7605-30-3, PHENYLSULFONYLACETIC ACID ETHYL ESTER

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Method for preparing beta-carbonyl sulfone
The invention discloses a method for preparing beta-carbonyl sulfone. The preparation method comprises the following steps: by taking an alpha-carbonyl diazo compound and sodium arylsulfinate as reaction substrates, cheap silver nitrate as an optimal catalyst, 1, 10-phenanthroline as a ligand and potassium persulfate as an oxidant, carrying out coupling reaction in a mixed solvent of acetonitrileand water to obtain the beta-carbonyl sulfone compound. Compared with the prior art, the method has the advantages of wide reaction substrate range, short reaction time, high reaction yield, mild reaction conditions and the like. Non-toxic and harmless reagents are used as reaction raw materials, so that the method is harmless to the environment and meets the requirements of modern green chemicaldevelopment. Post-reaction treatment is simple, and separation and purification are facilitated. In addition, the reaction can realize gram-scale synthesis, and lays a foundation for practical application.
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Paragraph 0018; 0019

(2020/03/12)

Cross coupling of sulfonyl radicals with silver-based carbenes: A simple approach to β-carbonyl arylsulfones
A coupling reaction between sulfonyl radicals and silver-based carbenes has been well established. This simple radical-carbene coupling (RCC) process provided an efficient approach to a variety of β-carbonyl arylsulfones from sodium arylsulfinates and diazo compounds, and was characterized by wide substrate scope, easy scale-up, simple manipulation, accessible starting materials, and mild reaction conditions.
Li, Jingjing,Lian, Pengcheng,Wan, Xiaobing,Wang, Hanghang,Zheng, Yonggao
supporting information
p. 2163 - 2169
(2020/03/27)

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
p. 4179 - 4188
(2019/05/08)

Tuning the solid-state emission of small push-pull dipolar dyes to the far-red through variation of the electron-acceptor group
Series of solid-state emitters based on the D-π-A dipolar structure and featuring various electron-donor and electron-acceptor groups were designed, and their spectroscopic properties studied. From weak emission in dilute solutions, intense emissions in aggregated state (AIE) and in the crystalline state were obtained. Analysis in light of crystal structures obtained by X-ray diffraction revealed specific crystal packing and presence of long chain of emitting aggregates. This simple molecular engineering around the D-π-A dipolar structure provides easy access to a wide range of effective solid-state emitters allowing modulation of emission wavelengths up to the near infrared (λem reaching 735 and 768 nm for compound 2f and 3f bearing the strongest electron-withdrawing group).
Redon, Sébastien,Eucat, Gwena?lle,Ipuy, Martin,Jeanneau, Erwann,Gautier-Luneau, Isabelle,Ibanez, Alain,Andraud, Chantal,Bretonnière, Yann
p. 116 - 132
(2018/04/16)

Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides
Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.
Fu, Ying,Xu, Qin-Shan,Li, Quan-Zhou,Du, Zhengyin,Wang, Ke-Hu,Huang, Danfeng,Hu, Yulai
supporting information
p. 2841 - 2845
(2017/04/03)

Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant
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.
Kupwade,Khot,Lad,Desai,Wadgaonkar
p. 6875 - 6888
(2017/10/06)

Bu4NI-Catalyzed Cross-Coupling between Sulfonyl Hydrazides and Diazo Compounds to Construct β-Carbonyl Sulfones Using Molecular Oxygen
A new cross-coupling reaction between sulfonyl hydrazides and diazo compounds has been established, leading to a variety of β-carbonyl sulfones in good yields. This methodology was distinguished by simple manipulation, easily available starting materials, and wide substrate scope. A plausible mechanism involving a radical process was proposed based upon the experimental observations and literature.
Wang, Yaxiong,Ma, Liang,Ma, Meihua,Zheng, Hao,Shao, Ying,Wan, Xiaobing
supporting information
p. 5082 - 5085
(2016/10/14)

Synthesis of diversely functionalised 2,2-disubstituted oxetanes: Fragment motifs in new chemical space
Di-, tri- and tetra-substituted oxetane derivatives with combinations of ester, amide, nitrile, aryl, sulfone and phosphonate substituents are prepared as fragments or building blocks for drug discovery. The synthesis of these novel oxetane functional groups, in new chemical space, is achieved via rhodium-catalysed O-H insertion and C-C bond forming cyclisation.
Davis, Owen A.,Croft, Rosemary A.,Bull, James A.
supporting information
p. 15446 - 15449
(2015/10/20)

An efficient electrochemical synthesis of β-keto sulfones from sulfinates and 1,3-dicarbonyl compounds
An efficient electrochemical synthesis of β-keto sulfones from sulfinates and 1,3-dicarbonyl compounds has been developed. The present electrochemical route could afford the target products in high to excellent yields under mild conditions.
Pan, Xiao-Jun,Gao, Jian,Yuan, Gao-Qing
p. 5525 - 5530
(2015/08/03)

PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS PDE9 INHIBITORS
A compound of the general formula (I) wherein R1 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, CN, -O-C1-C3-alkyl, fluorinated -O-C1-C3-alkyl, -(CH2)mOH and 5-membered heterocyclic group with 1 or 2 heteroatoms selected from N, O and S; and 6- or 10-membered heteroaryl with 1 to 3 heteroatoms selected from O, N and S; R2 and R3 independently of each other represent H atom or straight or branched C1-C3 alkyl; R4 is selected from the group consisting of 4- to 6- membered cycloalkyl, wherein one of carbon atoms can be replaced by O atom, and which is unsubstituted or substituted with one or two halogen atoms,and straight or branched C1-C4 alkyl; Q represents a bond or C1-C3-alkylene, which can be optionally substituted by one to three C1-C3-alkyls; X is selected from the group consisting of O, NR5, and S(O)p; R5 represents H atom or C1-C3alkyl; m is 1, 2 or 3; p is 0, 1 or 2; and salts thereof, for use as a medicament, in particular for treating cognitive function disorders and neurodegenerative diseases.
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(2014/02/16)

Design and synthesis of stable α-diazo-β-oxo sulfoxides
Diazo transfer adjacent to a sulfoxide moiety to provide stable, isolable α-diazo-β-oxo sulfoxides has been achieved. Use of monocyclic and bicyclic sulfoxide precursors is critical in enabling isolation of stable derivatives, through introduction of conformational constraint, while acyclic α-diazo-β-oxo sulfoxides are too labile to isolate and characterize.
Collins, Stuart G.,O'Sullivan, Orlagh C. M.,Kelleher, Patrick G.,Maguire, Anita R.
p. 1706 - 1725
(2013/03/29)

Selective oxidation of bulky sulfides to sulfoxides over titanosilicates having an MWW structure in the presence of H2O2 under organic solvent-free conditions
A selective hydrogen peroxide oxidation of sulfides to sulfoxides using Ti-MWW and Ti-IEZ-MWW catalysts was developed. This reaction was carried out under organic solvent-free conditions, and the only side-product was water. Improvement of catalytic activity toward bulky sulfides will be achieved by optimization of the topology in the Ti zeolite.
Kon, Yoshihiro,Yokoi, Toshiyuki,Yoshioka, Masato,Uesaka, Yumiko,Kujira, Harumi,Sato, Kazuhiko,Tatsumi, Takashi
supporting information
p. 4918 - 4921
(2013/09/02)

Synthesis and antimicrobial screening of some 3-(phenylsulfonyl)- 2H-chromen-2-ones
In this study, we have investigated the synthetic routes for the preparation of 3-sulfonyl coumarin 3 starting from phenylsulfonyl acetate 2 in the presence of mild base pyridine and piperidine and simple peroxide oxidation of sulphide 6 to sulfones 7 and their antimicrobial activities.
Edayadulla,Babu,Ramesh
p. 1 - 4
(2013/12/04)

Highly atom-economic, catalyst- and solvent-free oxidation of sulfides into sulfones using 30% aqueous H2O2
Highly atom-efficient oxidation of sulfides into sulfones under solvent- and catalyst-free reaction conditions using a 30% aqueous solution of H 2O2 at 75 °C is reported. A structurally diverse set of phenyl alkyl-, phenyl benzyl-, benzyl alkyl-, dialkyl-, heteroaryl alkyl- and cyclic sulfides were transformed into sulfones regardless of the aggregate state and electronic nature of the substituents. In spite of the heterogeneous reaction mixtures throughout the work, no difficulties with stirring and reaction progress were noted. In numerous cases, only 10 mol% excess of H 2O2 was used, thus contributing considerably to the high atom economy of the process. Some solid substrates required a variable excess of hydrogen peroxide; however, the reactions were performed strictly without organic solvents. The transformation was demonstrated to be amenable for scale-up with both liquid and solid sulfides. In addition, isolation and purification of the crude products can be simply done with only filtration and crystallization.
Jereb, Marjan
supporting information
p. 3047 - 3052,6
(2020/09/16)

Novel synthesis of pinacols and sulfones promoted by Smi￡ NiCl2 bimetallic system
Smi￡NiCl2 as a reductive system promoted reductive coupling of aryl adehydes and aryl ketone into pinacols in good yields and also promoted coupling reaction of aryl sulfonyl chlorides and active halides into sulfones in good yields.
Ye, Yuyuan,Zhou, Qizhong,Zheng, Renhua,Jiang, Huajiang,Chen, Rener,Zhang, Yongmin
experimental part
p. 331 - 334
(2012/05/04)

TiO2 nanoparticles and Preyssler-type heteropoly acid modified nano-sized TiO2: A facile and efficient catalyst for the selective oxidation of sulfides to sulfones and sulfoxides
A new and efficient synthetic method has been developed for the selective conversion of sulfides into their corresponding sulfones and sulfoxides using H2O2 in the presence of neat or Preyssler-type heteropoly acid modified nano-sized TiO2 as catalyst, respectively. The reaction was performed at room temperature with quantitative yields. The catalyst is reusable without significant loss of activity for the next oxidation reaction.
Rahimizadeh, Mohammad,Rajabzadeh, Ghadir,Khatami, Seyed-Mola,Eshghi, Hossein,Shiri, Ali
scheme or table
p. 59 - 64
(2010/09/04)

Formal aromatic C-H insertion for stereoselective isoquinolinone synthesis and studies on mechanistic insights into the C-C bond formation
(Chemical Equation Presented) Formal aromatic C-H insertion of rhodium(II) carbenoid was intensively investigated to develop a new methodology and probe its mechanism. Contrasting with the previously proposed direct C-H insertion, the mechanism was revealed to be electrophilic aromatic substitution, which was supported by substituent effects on the aromatic ring and a secondary deuterium kinetic isotope effect. Various isoquinolinones were synthesized intramolecularly via six-membered ring formation with high regioand diastereoselectivity, while averting the common Buchner-type reaction. Intermolecularly, dirhodium catalyzed formal aromatic C-H insertion on electron-rich aromatics was also achieved.
Park, Chan Pil,Nagle, Advait,Cheol, Hwan Yoon,Chen, Chiliu,Kyung, Woon Jung
supporting information; experimental part
p. 6231 - 6236
(2009/12/08)

Organic reactions in ionic liquids: An efficient method for the synthesis of aryl sulfones by alkylation of sodium arenesulfinates with alkyl halides
An ionic liquid based on 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF4) is used as a reusable reaction medium for the alkylation of sodium arenesulfinates with alkyl halides. This procedure is convenient, efficient and generally gives rise to the S-alkylated product with high selectivity when applied to active halides.
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
p. 267 - 269
(2007/10/03)

Tungstate-exchanged Mg-Al-LDH catalyst: An eco-compatible route for the oxidation of sulfides in aqueous medium
The catalytic oxidation of sulfides selectively to sulfoxides and/or sulfones is realised for the first time with heterogeneous tungstate-exchanged Mg-Al-LDH catalyst using 30% hydrogen peroxide in aqueous media at a faster rate in quantitative yields at room temperature. The heterogeneous catalyst showed higher activity (TOF) over its homogeneous analogues and other heterogeneous catalysts reported so far. The catalyst is well characterised by various instrumental techniques such as FT-IR spectroscopy, thermal analysis (TGA and DTA), powder XRD and chemical analysis. The catalyst is reused for six cycles with consistent activity and selectivity.
Choudary,Bharathi,Venkat Reddy,Lakshmi Kantam
p. 2069 - 2074
(2007/10/03)

Synthesis of sulfones from arenesulfonyl chlorides and alkyl halides using the Sm/HgCl2 bimetallic system
A simple and convenient procedure for the synthesis of sulfones from arenesulfonyl chlorides and alkyl halides using the Sm/HgCl2 bimetallic system in tetrahydrofuran is presented.
Zhang, Jiming,Zhang, Yongmin
p. 516 - 517
(2007/10/03)

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides
A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.
Aitken, R. Alan,Armstrong, Jill M.,Drysdale, Martin J.,Ross, Fiona C.,Ryan, Bruce M.
p. 593 - 604
(2007/10/03)

A convenient synthesis of sulfones using zinc mediated coupling reaction of sulfonyl chlorides with alkyl halides in aqueous media
An efficient procedure for the preparation of sulfones has been developed through a simple reaction of aromatic sulfonyl chlorides with suitable alkyl halides mediated by commercial zinc powder in aqueous media at 0 °C ~ room temperature.
Sun, Xinghua,Wang, Lei,Zhang, Yongmin
p. 1785 - 1791
(2007/10/03)

Indium-mediated Coupling Reaction of Sulfonyl Chlorides with Alkyl Bromides in Water. A Facile Synthesis of Sulfones
Indium-mediated coupling of alkyl bromides with aromatic sulfonyl chlorides gives the corresponding sulfones in aqueous media with moderate to good yields.
Wang, Lei,Zhang, Yongmin
p. 588 - 589
(2007/10/03)

A new methodology for obtaining α-oxo ester equivalents: Sulfanylation of α-sulfonyl carboxylic esters in a solid/liquid phase transfer catalytic system
A new, convenient procedure for the synthesis of a wide range of α-methylsulfanyl-α-phenylsulfonyl carboxylic esters has been developed and their facile conversion to the corresponding α-oxo esters demonstrated.
Wladislaw, Blanka,Marzorati, Liliana,Junior, Nelson Ferreira Claro,Di Vitta, Claudio
p. 420 - 422
(2007/10/03)

Effect of added benzoic acid on the phase-transfer catalysed permanganate oxidation of organosulfur compounds
The addition of benzoic acid in the oxidation of a range of sulfides and thiazolidinethiones using KMnO4 under phase-transfer conditions provides a convenient and high yielding procedure for formation of the corresponding sulfones, thiazolidinones and thiazolidinone S,S-dioxides.
Aitken, R. Alan,Mesher, Shaun T. E.,Ross, Fiona C.,Ryan, Bruce M.
p. 787 - 791
(2007/10/03)

α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms
Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.
Toyota, Akemi,Ono, Yoshinori,Chiba, Jun,Sugihara, Takumichi,Kaneko, Chikara
p. 703 - 708
(2007/10/03)

Selective synthesis of sulfoxides and sulfones by methyltrioxorhenium-catalyzed oxidation of sulfides with hydrogen peroxide
Methyltrioxorhenium-catalyzed oxidation of sulfides with hydrogen peroxide in ethanol has been found to be an efficient catalytic system for the selective formation of sulfoxides and sulfones. The oxidation using an equimolar amount of hydrogen peroxide afforded sulfoxides in excellent yield, and the use of two molar amounts of hydrogen peroxide gave sulfones quantitatively. Strongly deactivated sulfide, bis(4-nitrophenyl) sulfide, was converted smoothly to the corresponding sulfoxide and sulfone in excellent yields. The functional group in the side chain of sulfide such as a carbon-carbon double bond was not affected under the reaction conditions, and the sulfur atom was selectively oxidized.
Yamazaki, Shigekazu
p. 2955 - 2959
(2007/10/03)

The rhodium carbenoid route to oxazoles. Synthesis of 4-functionalised oxazoles; three step preparation of a bis-oxazole
Oxazole-4-sulfones, -phosphonates, and -nitriles are prepared by rhodium(II) catalysed addition of nitriles to the corresponding diazo compound. The effect of the ligand on rhodium was briefly investigated, with rhodium(II) trifluoroacetamide generally proving the most effective catalyst. The 4-cyanooxazole 9 is readily converted into the bis-oxazoles 10-12.
Doyle, Kevin J.,Moody, Christopher J.
p. 3761 - 3772
(2007/10/02)

Simple and efficient oxidation of sulfides to sulfones using catalytic ruthenium tetroxide
A procedure for the oxidation of sulfides to sulfones using ruthenium tetroxide as catalyst and periodic acid as stoichiometric oxidant in a biphasic system (CCl4, CH3CN, H2O) is reported.
Rodriguez, Carmen Ma,Ode, Jesus M.,Palazon, Jose Ma,Martin, Victor S.
p. 3571 - 3576
(2007/10/02)

A Novel Synthesis of Sulfones via the O,O-Diethylphosphorotellurite Ion-Assisted Coupling of Arenesulfonyl Chlorides with Active Halides
Arenesulfonyl chlorides undergo a facile onepot coupling reaction with active halides assisted by sodium O,O-diethylphosphorotellurite to give the corresponding sulfones in excellent yield.
Huang, Xian,Pi, Jin-Hong
p. 2291 - 2295
(2007/10/02)

Alkylation of Sodium Phenylsulfinate on Alumina. Activation by Microwaves or Ultrasounds.
Organic halides absorbed without solvent onto sodium phenylsulfinate on alumina (1) gave phenylsulfones (2) under microwave or ultrasound activation.
Villemin, Didier,Alloum, Abdelkrim Ben
p. 925 - 932
(2007/10/02)

Carboxylic acid derivatives, processes for the preparation thereof, the use thereof, and pharmaceutical compositions which contain these compounds
This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.
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(2008/06/13)

Chemistry of Novel Compounds with Multifunctional Carbon Structure. 5. Molecular Design of Versatile Building Blocks for Aliphatic Monofluoro Molecules by Manipulation of Multifunctional Carbon Structure
Three kinds of doubly functionalized monofluoromethylene fragments, 1-fluoro-1-nitro-1-(phenylsulfonyl)alkanes (10), 2-fluoro-2-(phenylsulfonyl)alkanoic esters (11), and 2-fluoro-2-nitroalkanoic esters (12), potentially versatile building blocks for the general synthesis of various aliphatic monofluoro molecules, were prepared from the corresponding difunctional compounds 1-3 by monoalkylation (R) and selective fluorinations.The interconversion or reductive removal of each functional group in 10-12 followed by the introduction of the second alkyl groups (R') at the fluorine-bearing carbon atom was examined.Compounds 12 proved to be useful and practical building blocks for conversions to the various monofluoroalkanes 20-26.
Takeuchi, Yoshio,Nagata, Kazuhiro,Koizumi, Toru
p. 5453 - 5459
(2007/10/02)

CHEMICAL MODIFICATION OF POLY-VINYLBENZYLTRIPHENYLPHOSPHONIUM SALTS AND THEIR APPLICATIONS AS REAGENTS IN ORGANIC SYNTHESIS
Insoluble polymer-bound reagents derived from poly(vinylbenzyltriphenylphosphonium salts) have been prepared and used as reagents in organic synthesis.The polymer-supported borohydride was used as reducing agent towards carbonyl compounds.The reaction of polymer-supported thiocyanate and nitrile anions with alkyl halides in hydrocarbon solvents gave good yields of the corresponding alkyl thiocyanates and nitroalkanes, respectively.In addition, polymer-bound carboxylate, phenoxide, and sulfinate anions were used for the synthesis of esters, ethers, and sulfones by reaction with alkyl halides in non-polar solvents.
Akelah, Ahmed,Abdel Galil, Fathy M.
p. 91 - 96
(2007/10/02)