Session S23a (Monday, 9:30am, Life Sciences 011)

P163: Aerobic oxidation of alcohols using a Cu/TEMPO catalyst

Nicholas Hill, Jessica Hoover, Shannon Stahl (University of Wisconsin – Madison, USA)

Modern undergraduate organic chemistry textbooks typically provide detailed discussion of stoichiometric Cr- and Mn-based reagents for the oxidation of alcohols.  However, the use of such oxidants in the organic instructional laboratory is increasingly discouraged on account of their toxicity and the requirement for their presence in stoichiometric amounts.  The development of catalytic systems that enable atmospheric oxygen to be used as the oxidant is an area of intense contemporary research.  This paper describes a laboratory exercise that uses a catalyst system consisting of CuBr, TEMPO, and 2,2′-bipyridine for the efficient aerobic oxidation of benzyl alcohols to the corresponding aldehydes.  The protocol is adapted from the current research literature (J. M. Hoover and S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 16901-16910) and provides students with practical experience of a modern, green oxidation method while encouraging the discussion and exploration of metal-based catalytic reactions.

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