Reduction of ketones to alcohols using a decaborane/pyrrolidine/cerium(III) chloride system in methanol
Jong Woo Bae, Seung Hwan Lee, Yeon Joo Jung, Choon-Ock Maing Yoon and Cheol Min Yoon*
*Department of Life Science & Biotechnology, Graduate school of
Biotechnology, Korea University, 1, 5-Ka, Anam-Dong Sungbuk-Ku, Seoul, 136-701
Korea, Email: cmyoon
korea.ac.kr
J. W. Bae, S. H. Lee, Y. J. Jung, C.-O. M. Yoon, C. M. Yoon, Tetrahedron Lett., 2001, 42, 2137-2139.
DOI: 10.1016/S0040-4039(01)00005-3
Abstract
Decaborane was found to be an effective agent for the chemoselective reduction of ketones to alcohols in the presence of pyrrolidine and cerium(III) chloride heptahydrate in methanol.
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The document discusses a study on the reduction of ketones to alcohols using a decaborane:pyrrolidine:cerium(III) chloride system in methanol. The research, conducted by Jong Woo Bae and colleagues at Korea University, found that decaborane is an effective agent for the chemoselective reduction of ketones in the presence of pyrrolidine and cerium(III) chloride heptahydrate. The optimal conditions involved using 30 mol% of decaborane, 30 mol% of pyrrolidine, and 10 mol% of cerium(III) chloride heptahydrate at around 50°C. The study showed that without cerium chloride, the reaction did not proceed, and the addition of pyrrolidine improved the yield significantly. Secondary amines like pyrrolidine and piperidine were more efficient than triethylamine and pyridine. The reaction was compatible with various functional groups such as nitro, ester, and bromide, and did not reduce the double bond in conjugated ketones. The process was completed within 8 hours, yielding high amounts of the corresponding alcohols. This method offers a mild and efficient approach for ketone reduction in organic synthesis. The research was supported by the Korea Science and Engineering Foundation.
Key Words
Luche reduction, reduction of ketones, decaborane, pyrrolidine, cerium chloride heptahydrate, alcohol, decaborane
ID: J72-Y2001-380
