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Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry

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Sulfonyl radical mediated processes have been considered as a powerful strategy for the construction of sulfonyl compounds. However, an efficient and high atom-economical radical approach to the synthesis of sulfonate… Click to show full abstract

Sulfonyl radical mediated processes have been considered as a powerful strategy for the construction of sulfonyl compounds. However, an efficient and high atom-economical radical approach to the synthesis of sulfonate esters is still rare, owing to the limited tactics to achieve alkoxysulfonyl radicals. Herein, an electrochemical anodic oxidation of inorganic sulfites with alcohols is developed to afford alkoxysulfonyl radical species, which are utilized in subsequent alkene difunctionalization to provide various sulfonate esters. This transformation features excellent chemoselectivity and broad functional group tolerance. This new discovery presents the potential prospect for the construction of sulfonate esters, and enriches the electrochemical reaction type.

Keywords: alkoxysulfonyl radical; species acquisition; radical species; electrochemistry; sulfonate esters; transformation

Journal Title: Chemical Science
Year Published: 2022

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