title: Highly practical copper(I)/TEMPO catalyst system for chemoselective aerobic oxidation of primary alcohols.
abstract: Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, such as the use of pure O(2) as the oxidant or complex catalyst synthesis. Here, we report a new (bpy)Cu(I)/TEMPO catalyst system that enables 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 the high selectivity for 1° alcohols enables selective oxidation of diols that lack protecting groups.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, Wisconsin 53706, USA.
authors.forename: Jessica M
authors.initials: JM
authors.lastname: Hoover
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000438:Alcohols; D003497:Cyclic N-Oxides; D003300:Copper; C003959:TEMPO