ABSTRACT
Setrak K. Tanielyan1, Robert L. Augustine1 , Clementina Reyes1, Nagendranath Mahata1, Michael Korell2, Oliver Meyer3
1Center for Applied Catalysis, Seton Hall University, South Orange,NJ 07079
2Degussa Corp., BU Building Blocks, Parsippany, NJ 07054 3Degussa AG, BU Building Blocks, Marl 45764, Germany
tanielse@shu.edu
Abstract
The oxidation of alcohols to the corresponding aldehydes, ketones or acids represents one of the most important functional group transformations in organic synthesis. While this is an established reaction, it still presents an important challenge (1). Although there are numerous oxidation methods reported in the literature, only a few describe the selective oxidation of primary or secondary alcohols to the corresponding aldehydes or ketones utilizing TEMPO based catalyst systems in combination with clean oxidants such as O2 and H2O2 (2). The most efficient, common, TEMPO based systems require the use of substantial amounts of expensive and/or toxic transition metal complexes, which makes them unsuitable for industrial scale production. Here, we report a highly effective aerobic oxidation of primary and secondary alcohols by a catalyst system, based on 4-acetamido-2,2,6,6tetramethylpiperidin-1-oxyl (AA TEMPO), Mg(NO3)2 and N-bromosuccinimide (NBS) in an acetic acid solvent.
