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Hypervalent Iodine-Mediated Synthesis of Sulfinimidate Esters from Sulfenamides.

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In this study, we present a novel and efficient approach for the oxidative esterification of sulfenamides using phenyliodonium diacetate, enabling the synthesis of sulfinimidate esters and sulfilimines under mild and… Click to show full abstract

In this study, we present a novel and efficient approach for the oxidative esterification of sulfenamides using phenyliodonium diacetate, enabling the synthesis of sulfinimidate esters and sulfilimines under mild and metal-free conditions, with yields reaching up to 99%. The protocol is readily scalable and compatible with a diverse range of substrates and functional groups, and we demonstrate its potential for late-stage functionalization of pharmacologically relevant molecules. Furthermore, we propose a plausible reaction mechanism to account for the observed sequence of events.

Keywords: sulfinimidate esters; synthesis sulfinimidate; hypervalent iodine; iodine mediated

Journal Title: Organic letters
Year Published: 2023

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