(tert-Butoxyimino)-λ⁴-sulfanone

References

• 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.
• 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.

Used Chemicals

• (tert-Butoxyimino)-λ⁴-sulfanone (= tBuONSO) [U0150]
• p-Tolylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L) [T1700]
• THF (anhydrous)

Procedure

To a solution of tBuONSO (400 mg, 2.96 mmol), in THF (anhydrous, 12 mL) was added p-tolylmagnesium bromide (19% in tetrahydrofuran, ca. 1mol/L, 4.4 mL, 4.4 mmol) at -78 °C and the mixture was stirred at -78 °C for 1 hour. The suspension was warmed at room temperature and stirred for overnight. After that, methanol (1 mL) was add to the reaction mixture and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane = 0:1 - 1:4 on silica gel) to give 4-methylbenzenesulfonamide as a white solid (407 mg, 80%).

Experimenter’s Comments

The reaction mixture was monitored by UPLC.

Analytical Data

4-Methylbenzenesulfonamide

¹H NMR (400 MHz, CDCl₃); δ 7.70 (d, 2H, J = 8.4 Hz), 7.36 (d, 2H, J = 8.1 Hz), 7.27 (brs, 2H), 2.33 (s, 3H).

Lead Reference

• 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.