Reagent for Primary Sulfonamide Synthesis

tBuONSO (1) is utilized as a reagent for primary sulfonamide synthesis. 1 reacts with Grignard reagents or organolithium reagents to give sulfonamides via nucleophilic attack on the sulfur atom of 1 and successive elimination of isobutene. Organometallic reagents with various carbon skeletons such as aryl, heteroaryl, cyclopropyl, even sterically hindered isopropyl and tert-butyl groups are applicable.

Related Products

U0150

(tert-Butoxyimino)-λ⁴-sulfanone (= tBuONSO)

B3960

Bis(sulfur Dioxide)-1,4-diazabicyclo[2.2.2]octane Adduct (= DABSO)

U0113

Sulfur Dioxide 1-Methylpyrrolidine Adduct (= TIMSO)

T3773

(Triphenylmethyl)thionyl Imide (= TrNSO)

References

• 1) Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO
  • T. Q. Davies, M. J. Tilby, D. Skolc, A. Hall, M. C. Willis, Org. Lett. 2020, 22, 9495.
• 2) Direct one step dehydrogenative C-H sulfonimidation of unfunctionalized arenes: A conveneient protocol to emerging medicinal chemistry motifs without prefunctionalized arenes
  • S. Tummanapalli, K. C. Gulipalli, S. Bodige, D. Vemula, S. Endoori, A. K. Pommidi, S, K. Punna, Tetrahedron Lett. 2021, 73, 153118.

Page Top