28925-53-3Relevant articles and documents
Method for synthesizing alpha-sulfone ketone compound from alpha, alpha-dibromo ketone by one-pot process
-
Page/Page column 9; 10, (2019/10/17)
The invention discloses a method for synthesizing a high-added-value alpha-sulfone ketone compound from an alpha, alpha-dibromo ketone compound by a one-pot process. The method has the advantages thatan alpha-sulfone ketone derivative is synthesized from alpha, alpha-dibromo ketone, which is simple and easy to obtain, by the one-pot process without separation of an alpha-bromo ketone intermediate, so that a separation process for an intermediate product is omitted, the steps are reduced, and requirements for environment protection are met; the steps of the method are simple and easy to operate, no transition metal reagents are required, and economical sulfonate with less pollution is directly used as a promoter and a sulfonating agent for reducing debromination of the alpha, alpha-dibromoketone, so that the cost is reduced, and economic benefits of reactions are increased; a system for preparing the alpha-sulfone ketone derivative by the one-pot process is developed to provide a novel synthesis method for preparation of the alpha-sulfone ketone compound, and the method has good industrialization prospect and potential application value.
NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates
Muneeswara, Madithedu,Sundaravelu, Nallappan,Sekar, Govindasamy
, p. 3479 - 3484 (2019/05/21)
An efficient synthetic route towards the synthesis of β-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, α-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility.
Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones
Deng, Siqi,Liang, En,Wu, Yinrong,Tang, Xiaodong
supporting information, p. 3955 - 3957 (2018/09/27)
The oxidative sulfonylation of ketones with sodium sulfinates as the sulfone source and DMSO as the oxidant is reported. A series of β-keto sulfones were obtained in good to excellent yields. The advantages of this efficient protocol include the low cost of DMSO and HBr, and a broad scope.
Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds
Chen, Jiajia,Guo, Wei,Wang, Zhenrong,Hu, Lin,Chen, Fan,Xia, Yuanzhi
, p. 5504 - 5512 (2016/07/13)
The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.
ISOSELECTIVITY RELATIONSHIP IN THE "HALOGENOPHILIC" REACTION OF α-CHLORODESYL ARYL SULFONES WITH SODIUM THIOPHENOLATES
Karavan, V. S.,Simonov, D. A.,Novikov, M. S.
, p. 812 - 816 (2007/10/02)
In reaction with sodium thiophenolate in methanol in the presence of an equimolar excess of thiophenol, α-chlorodesyl aryl sulfones are reduced to the corresponding sulfones.It was established that the nature of the "structure-selectivity" relationship is
Selenosulfonation of Acetylenes: Preparation of Novel β-(Phenylseleno)vinyl Sulfones and Their Conversion to Acetylenic and β-Functionalized Sulfones
Back, Thomas G.,Collins, Scott,Kerr, Russell G.
, p. 3077 - 3084 (2007/10/02)
The 1,2-additions of Se-phenyl p-tolueneselenosulfonate (1) to acetylenes under mild conditions afford β-(phenylseleno)vinyl sulfones 3, generally in high yields.The reaction is highly regioselective (anti-Markovnikov) and stereoselective (anti) and proceeds via a free-radical chain mechanism initiated by the thermolysis of the selenosulfonate.The oxidation of β-(phenylseleno)vinyl sulfones with m-chloroperbenzoic acid generates the corresponding selenoxides 4, which undergo syn or base-catalyzed elimination to furnish acetylenic sulfones 5.Base-catalyzed alcoholyses of selenoxides 4 in methanol or ethylene glycol produce β-keto sulfone ketals 8 or 10, respectively.Free β-keto sulfones 11 are formed by the acid-catalyzed hydrolysis of the corresponding β-(phenylseleno)vinyl sulfones 3.
