Bismuth Tribromide Catalyzed Oxidation of Alcohols with Aqueous Hydrogen Peroxide

Abstract

An efficient bismuth tribromide catalyzed oxidation of various alcohols with aqueous hydrogen peroxide is described, leading to the corresponding carbonyl compounds.

Key words

alcohols - catalysis - green chemistry - oxidation - hydrogen peroxide

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• 30 General Experimental Procedure for the Oxidation of Alcohols: To a solution of the alcohol (1.0 mmol) and hydrogen peroxide (5.0 mmol, 30% aq) was added BiBr₃ (10 mol%). The reaction mixture was stirred at 70 °C for 10–40 min, and the reaction mixture was extracted with dichloromethane (2 × 5 mL). The combined organic layers were washed with saturated brine (2 × 5 mL) and dried with anhydrous MgSO₄. After evaporation of the solvent, the residue was purified by flash column chromatography (SiO₂; CH₂Cl₂–hexane, 3:2) to afford the pure carbonyl compound. 4-Methylbenzaldehyde (Table 1, entry 3): colorless oil; 111 mg (92% yield). ¹H NMR (300 MHz, CDCl₃): δ = 9.94 (s, 1 H), 7.76 (d, J = 8.1 Hz, 2 H), 7.32 (d, J = 8.1 Hz, 2 H), 2.42 (s, 3 H). Benzophenone (Table 1, entry 18): off-white solid; 155 mg (85% yield). ¹H NMR (300 MHz, CDCl₃): δ = 7.68 (m, 4 H), 7.51–7.40 (m, 2 H), 7.39–7.29 (m, 4 H).