5366-49-4Relevant academic research and scientific papers
Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
Dar'In, Dmitry,Kantin, Grigory,Bakulina, Olga,Krasavin, Mikhail
, p. 2259 - 2266 (2020/08/26)
A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.
Method for synthesizing beta-carbonyl sulfone compound
-
Paragraph 0016; 0017, (2019/06/13)
The invention discloses a method for synthesizing a beta-carbonyl sulfone compound. The method comprises the steps that sulfinate and a carbonyl compound containing alpha-position active hydrogen areused as raw materials, in a solvent, under the oxidation of alkali, sodium iodide, nanomicelle and 1,2-dibromoethane, the reaction is carried out at 60-80 DEG C for 10-12 hours, separation and purification are performed, and the beta-carbonyl sulfone compound is obtained. The method is simple in synthesis process, convenient in operation, mild in reaction condition, low in cost and high in yield,does not use transition metal catalysis, and is green and safe.
Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions
Lozovskiy, Stanislav V.,Ivanov, Alexander Yu.,Khoroshilova, Olesya V.,Vasilyev, Aleksander V.
supporting information, p. 2897 - 2906 (2018/12/13)
In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.
PQS-enabled visible-light iridium photoredox catalysis in water at room temperature
Bu, Mei-Jie,Cai, Chun,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 1233 - 1237 (2018/03/26)
An amphoteric PQS-attached photocatalyst has been prepared that undergoes self-aggregation in water into nanomicelles. This covalently bound species enables Ir-based photoredox catalysis to be conducted in the absence of additives or co-solvents. Representative reactions are described using this new catalytic system, which require no additional investment of external energy in the form of heating or cooling. The entire aqueous reaction mixture readily undergoes in-flask recycling and thus, represents a sustainable precious metal technology.
Copper-Catalyzed Oxidative Reaction of β-Keto Sulfones with Alcohols via C?S Bond Cleavage: Reaction Development and Mechanism Study
Du, Bingnan,Wang, Wenmin,Wang, Yang,Qi, Zhenghang,Tian, Jiaqi,Zhou, Jie,Wang, Xiaochen,Han, Jianlin,Ma, Jing,Pan, Yi
supporting information, p. 404 - 408 (2018/02/21)
A Cu-catalyzed cascade oxidative radical process of β-keto sulfones with alcohols has been achieved by using oxygen as an oxidant. In this reaction, β-keto sulfones were converted into sulfinate esters under the oxidative conditions via cleavage of C?S bond. Experimental and computational studies demonstrate that a new pathway is involved in this reaction, which proceeds through the formation of the key four-coordinated CuII intermediate, O?O bond homolysis induced C?S bond cleavage and Cu-catalyzed esterification to form the final products. This reaction provides a new strategy to sulfonate esters and enriches the research content of C?S bond cleavage and transformations.
O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
Katrun, Praewpan,Songsichan, Teerawat,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
supporting information, p. 1109 - 1121 (2017/02/24)
A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.
An efficient electrochemical synthesis of β-keto sulfones from sulfinates and 1,3-dicarbonyl compounds
Pan, Xiao-Jun,Gao, Jian,Yuan, Gao-Qing
, p. 5525 - 5530 (2015/08/03)
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.
Chemoselective one-pot synthesis of β-keto sulfones from ketones
Rawat, Vikas S.,Reddy, Perla L. M.,Sreedhar, Bojja
, p. 5165 - 5168 (2014/01/23)
A practical method to synthesize substituted β-keto sulfones directly from ketones at room temperature has been developed. This method involves the nucleophilic addition of a base generated enolate to sulfonyl iodide. The reaction shows high chemoselectivity for the addition of a sulfonyl group to an α-carbon over a hydroxyl group. In addition, the given protocol provides good to excellent yields of β-keto sulfones under mild reaction conditions. Moreover, the regiochemical aspect of the protocol is also explored.
METHOD FOR PRODUCING PYRIDAZINONE COMPOUNDS AND INTERMEDIATE THEREOF
-
Page/Page column 307, (2012/03/27)
The present invention relates to a novel method for producing a pyridazinone compound and an intermediate thereof as shown in the following scheme: wherein the symbols are as defined in the specification.
(Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles
Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.,Obushak, Mykola D.
scheme or table, p. 2321 - 2323 (2010/02/16)
β-Keto sulfones and b-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. Georg Thieme Verlag Stuttgart.
