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Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: alleviating steric and electronic constraints of Cu/TEMPO catalyst systems.

Journal of the American Chemical Society (2013-10-17)
Janelle E Steves, Shannon S Stahl
ABSTRACT

Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of ((MeO)bpy)Cu(I)(OTf) and ABNO ((MeO)bpy = 4,4'-dimethoxy-2,2'-bipyridine; ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl), that mediates aerobic oxidation of all classes of alcohols, including primary and 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 the source of oxidant.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
9-Azabicyclo[3.3.1]nonane N-oxyl, 95%
Pricing and availability is not currently available.
Sigma-Aldrich
Stahl Aerobic Oxidation ABNO solution, 0.04M ABNO in Acetonitrile, Solution for Oxidation of Primary and Secondary Alcohols
Pricing and availability is not currently available.

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