Davies TQ,
Tilby MJ,
Skolc D,
Hall A,
Willis MC.
*
University of Oxford, UK
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
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.
