- Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
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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.
- Dar'In, Dmitry,Kantin, Grigory,Bakulina, Olga,Krasavin, Mikhail
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p. 2259 - 2266
(2020/08/26)
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- Copper-Catalyzed Oxidative Reaction of β-Keto Sulfones with Alcohols via C?S Bond Cleavage: Reaction Development and Mechanism Study
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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.
- Du, Bingnan,Wang, Wenmin,Wang, Yang,Qi, Zhenghang,Tian, Jiaqi,Zhou, Jie,Wang, Xiaochen,Han, Jianlin,Ma, Jing,Pan, Yi
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supporting information
p. 404 - 408
(2018/02/21)
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- (Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles
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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.
- Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.,Obushak, Mykola D.
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scheme or table
p. 2321 - 2323
(2010/02/16)
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- Hypervalent iodine in synthesis. 66. One pot preparation of β-keto sulfones by reaction of ketones, [hydroxy(tosyloxy) iodo] benzene, and sodium sulfinates
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One pot reactions of ketones, [hydroxy(tosyloxy)iodo] benzene and sodium sulfinates lead to the formation of the corresponding β-keto sulfones under mild conditions and in good yield.
- Xie,Chen
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p. 3145 - 3149
(2007/10/03)
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- RAPID AMD LARGE-SCALE SYNTHESIS OF SULFONYL-SUBSTITUTED PROPANONES
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A one-pot, large-scale, and rapid (10-20 minutes) synthesis of sulfonyl-substituted propanone has been developed.The synthesis, starting with a thiol, chloroacetone, and OXONE, can easily be monitored with the use of a pH indicator.
- Davis, Roman
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p. 823 - 828
(2007/10/02)
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