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Synlett 2007(4): 0643-0645  
DOI: 10.1055/s-2007-967969
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Simple, Efficient and Recyclable Copper(II) Acetylacetonate Catalytic System for Oxidation of sec-Alcohols in Ionic Liquid

Chong Liu, Jinyu Han*, Juan Wang
Key Laboratory for Green Chemical Technology of State Education Ministry, School of Chemical Engineering & Technology, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27890859; e-Mail: hanjinyu@tju.edu.cn;
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Publication History

Received 24 November 2006
Publication Date:
21 February 2007 (online)

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Abstract

A selective oxidation of secondary alcohols to the corresponding ketones in room temperature ionic liquid was achieved by using copper acetylacetonate/tert-butylhydroperoxide system. The catalytic system can be recycled and reused for five runs without any significant loss of catalytic activity and products are obtained in excellent yield.

Key words

copper acetylacetonate - oxidation - sec-alcohols - ionic liquid - catalyst

17

Representative Procedure for the Oxidation of Secondary Alcohols. A mixture of cyclohexanol (2 mmol), copper acetylacetonate [Cu(acac)2, 0.06 mmol] and t-BuOOH (10 mmol) was added in a microreactor under magnetic stirring for 1 min, and [bmim]PF6 (1 mL) was added to the mixture. After 10 min of stirring, the blue color of the reaction mixture turned into dark green color. The reaction mixture was stirred at r.t. for 5 h and then extracted with n-hexane (3 × 5 mL). The combined n-hexane phase was concentrated in vacuo and monitored by GC and 1H NMR. Then the residue was purified by flash chromatography to afford cyclohexanone (51% yield).