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Preparation of Primary Sulfonamides by t-BuONSO and Organometallics
Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO.
Org. Lett. 2020;
Willis and co-workers report the reaction of readily available organometallic reagents and the novel sulfinylamine reagent t-BuONSO [N-sulfinyl-O-(tert-butyl)hydroxylamine] for the direct synthesis of primary sulfonamides in good yields.
The authors proposed a reaction mechanism in which, after nucleophilic attack of the Grignard reagent, the sulfinamide A was formed. This intermediate was converted into B, either via a sulfinyl nitrene intermediate or by a concerted N → S O migration. After an intermolecular proton transfer, isobutene was eliminated, giving the anion C, which was quenched after work-up to yield the desired sulfonamide.
20 January 2021 (online)
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