Synlett 2015; 26(17): 2434-2436
DOI: 10.1055/s-0035-1560467
letter
© Georg Thieme Verlag Stuttgart · New York

Bismuth Tribromide Catalyzed Oxidation of Alcohols with Aqueous Hydrogen Peroxide

Mi-kyung Han
Department of Chemistry, Chung-Ang University, Seoul 156-756, Republic of Korea   Email: jclee@cau.ac.kr
,
Sohwa Kim
Department of Chemistry, Chung-Ang University, Seoul 156-756, Republic of Korea   Email: jclee@cau.ac.kr
,
Sung Tae Kim
Department of Chemistry, Chung-Ang University, Seoul 156-756, Republic of Korea   Email: jclee@cau.ac.kr
,
Jong Chan Lee*
Department of Chemistry, Chung-Ang University, Seoul 156-756, Republic of Korea   Email: jclee@cau.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 14 July 2015

Accepted after revision: 07 August 2015

Publication Date:
02 September 2015 (online)


Abstract

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

 
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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).