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TCI Practical Example: Oxidation Reaction Using Triphenylantimony as a Catalyst

We are proud to present the air oxidation of furoin to furil catalyzed by triphenylantimony.

Used Chemicals

• Furoin [F0082]
• Triphenylantimony [T0476]
• Dichloromethane

Procedure

A Solution of furoin (500 mg, 2.6 mmol) and triphenylantimony (92 mg, 0.3 mmol) in dichloromethane (10 mL) was stirred under air atmosphere at room temperature for 17 hours. The reaction mixture was removed under reduced pressure and the crude was purified by silica gel column chromatography (hexane:ethyl acetate = 3:1, Rf = 0.36) to give furil as a yellow solid (466 mg, 94% yield).

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane:ethyl acetate = 3:1, Rf = 0.36).

Analytical Data

Furil

¹H NMR (270 MHz, CDCl₃); δ 7.79 (d, J = 1.6 Hz, 2H), 7.65 (d, J = 3.8 Hz, 2H), 6.65 (dd, J = 3.5, 1.6 Hz, 2H)

Lead Reference

• Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition
• • S. Yasuike, Y. Kishi, S. Kawara, J. Kurita, Chem. Pharm. Bull. 2005, 53, 425.