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DOI: 10.1055/s-0040-1706668
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;
22: 9495-9499
DOI: 10.1021/acs.orglett.0c03505.
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Significance
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.
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Comment
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.
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Publication History
Article published online:
20 January 2021
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