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TCI Practical Example: Sulfoximination Using the Iodonium Ylide Reagent

We are proud to present the synthesis of sulfoximine using an iodonium ylide reagent PhINTs as a nitrene source.

Used Chemicals

• [N-(p-Toluenesulfonyl)imino]phenyliodinane (= PhINTs) [T3967]
• Methyl Phenyl Sulfoxide [M1148]
• Copper(II) Trifluoromethanesulfonate [T1292]
• Acetonitrile

Procedure

To a solution of copper(II) trifluoromethanesulfonate (52 mg, 0.14 mmol) in acetonitrile (10 mL) was successively added methyl phenyl sulfoxide (0.20 g, 1.4 mmol) and PhINTs (0.59 g, 1.6 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was stirred for 5 hours, then the solvent was removed under reduced pressure. The crude mixture was purified by column chromatography (ethyl acetate:hexane = 1:2 on silica gel), giving compound 1 as a white powder (0.31 g, 70% yield).

Experimenter’s Comments

The reaction mixture was monitored by ¹H NMR (DMSO-d₆).
PhINTs must be kept cool and be avoided contact with some of organic solvents (ex. THF) due to its high reactivity.

Analytical Data

Compound 1

¹H NMR (400 MHz, CDCl₃); δ 8.02 (d, 2H, J = 7.3 Hz), 7.86 (d, 2H, J = 8.2 Hz), 7.71 (t, 1H, J = 7.6 Hz), 7.61 (dd, 2H, J = 7.6, 8.2 Hz), 7.26 (d, 2H, J = 8.2 Hz), 3.43 (s, 3H), 2.40 (s, 3H).

¹³C NMR (101 MHz, CDCl₃); δ 143.0, 140.7, 138.4, 134.5, 129.9, 129.4, 127.6, 126.8, 46.8, 21.7.

Lead Reference

• Catalytic Synthesis of Sulfoximines using Copper(II) Salts
• E. Lacôte, M. Amatore, L. Fensterbank, M. Malacria, Synlett 2002, 116.

Other Reference

• [N-(p-Toluenesulfonyl)imino]phenyliodinane
• D. A. Evans, D. A. Barnes, e-EROS 2001.