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TCI Practical Example: Oxidation Reaction of Heterocycles Using Iodobenzene Diacetate

We are proud to present the oxidation reaction of 2-phenylimidazoline using iodobenzene diacetate as an oxidant.

Used Chemicals

• Iodobenzene Diacetate (= PIDA) [I0330]
• 2-Phenylimidazoline [P0685]
• Potassium Carbonate [P1748]
• Dimethyl Sulfoxide

Procedure

Iodobenzene diacetate (1.21 g, 3.8 mmol, 1.1 eq.) was added to a solution of 2-phenylimidazoline (500 mg, 3.4 mmol) and potassium carbonate (520 mg, 3.8 mmol, 1.1 eq.) in DMSO (17 mL) and the reaction mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate (75 mL) and washed with saturated aqueous sodium bicarbonate solution (2 x 50 mL), then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on aminosilica gel, ethyl acetate:hexane = 0:1 - 1:0) to give 2-phenylimidazole as a white solid (340 mg, 69% yield).

Experimenter's Comments

The reaction mixture was monitored by NH-TLC (ethyl acetate, Rf = 0.30).

Analytical Data

2-phenylimidazole

¹H NMR (270 MHz, DMSO-d₆); δ 12.5 (dr, 1H), 7.95-7.91 (m, 2H), 7.44 (t, 2H, J = 7.3 Hz), 7.33 (t, 1H, J = 7.3 Hz), 7.24 (s, 1H), 7.02 (s, 1H)

Lead Reference

• Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with pharmaceutically-relevant heterocycles
  • J. Atzrodt, V. Derdau, W. J. Kerr, M. Reid, P. Rojahn, R. Wecka, Tetrahedron 2015, 71, 1924.