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

Jessica M. Hoover and Shannon S. Stahl*

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

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

DOI: 10.1021/ja206230h

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Abstract

A (bpy)CuI/TEMPO catalyst system enables an efficient and selective aerobic oxidation of a broad range of primary alcohols, including allylic, benzylic, and aliphatic derivatives, to the corresponding aldehydes using readily available reagents, at room temperature with ambient air as the oxidant. The catalyst system is compatible with a wide range of functional groups and shows a high selectivity for 1° alcohols.

see article for more examples

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

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

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Key Words

Aldehydes, Oxygen

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ID: J48-Y2011-3070