Aerobic alcohol oxidation reactions are appealing and have broad potential utility, but they are seldom used in bench-scale and industrial chemistry due to limited reaction scope and/or safety concerns.  Our laboratory recently disclosed a highly practical Cu/TEMPO catalyst system for aerobic alcohol oxidation that exhibits very high selectivity for primary alcohols and good functional group tolerance (Hoover & Stahl J. Am. Chem. Soc. 2011 , 133, 16901-16910).  A subsequent mechanistic study of this catalyst system (Hoover et al. J. Am. Chem. Soc. 2013 , 135, 2357-2367) has provided valuable insights for the development of improved catalyst systems that enable significantly higher catalytic turnover rates with aliphatic alcohols and efficient oxidation of secondary alcohols. This presentation will describe our mechanistically-guided approach to the discovery of the new catalyst systems.

Mild and practical copper-catalyzed aerobic oxidation of primary and secondary alcohols

246th National Meeting (2013)

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