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 oxidantsстатья

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Дата последнего поиска статьи во внешних источниках: 14 августа 2019 г.

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[1] 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 / O. M. Mulina, D. A. Pirgach, G. I. Nikishin, A. O. Terent’ev // European Journal of Organic Chemistry. — 2019. — Vol. 2019, no. 26. — P. 4179–4188. Selectivity of sulfonylation of β-ketoesters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by a type of a solvent and reaction temperature. α-Sulfonyl β-ketoesters are obtained when the process is conducted in THF:H2O solution at 40 oC. The change of the solvent to i-PrOH: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. [ DOI ]

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