Preparation of Primary Sulfonamides by t-BuONSO and Organometallics

Key words

sulfonamides - Grignard reagents - organometallics

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.

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.

Publication History

Article published online:
20 January 2021