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Highly practical copper(I)/TEMPO catalyst system for chemoselective aerobic oxidation of primary alcohols.

Journal of the American Chemical Society (2011-08-25)
Jessica M Hoover, Shannon S Stahl
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Stahl Aerobic Oxidation TEMPO solution, 0.2 M in acetonitrile, Solution for Oxidation of Primary Alcohols
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