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Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems

Janelle E. Steves and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

J. E. Steves, S. S. Stahl, J. Am. Chem. Soc., 2013, 135, 15742-15745.

DOI: 10.1021/ja409241h (free Supporting Information)


Abstract

Cu/TEMPO catalyst systems show reduced reactivity in aerobic oxidation of aliphatic and secondary alcohols. A catalyst system consisting of (MeObpy)CuOTf and ABNO mediates aerobic oxidation of primary, secondary allylic, benzylic, and aliphatic alcohols with nearly equal efficiency. The catalyst exhibits broad functional group compatibility, and most reactions are complete within 1 h at room temperature using ambient air as oxidant.

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Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols

J. M. Hoover, S. S. Stahl, J. Am. Chem. Soc., 2011, 133, 16901-16910.


Key Words

aldehydes, ketones, 9-Azabicyclo[3.3.1]nonane N-Oxyl, oxygen


ID: J48-Y2013