Synfacts 2021; 17(02): 0161
DOI: 10.1055/s-0040-1706668
Metals in Synthesis

Preparation of Primary Sulfonamides by t-BuONSO and Organometallics

Contributor(s):
Paul Knochel
,
Alexander Kremsmair
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.
 

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

Publication Date:
20 January 2021 (online)

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