Selective Electrochemical Oxidation of Alcohols Catalyzed by Partially Biobased TEMPO Analogs**

Abstract

A new electrochemical catalyst has been synthesized from an analog of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and the medium chain fatty acid, undecenoic acid. The electrochemical properties of the new material are shifted to more positive potential by ∼ 170 mV, typical for other substituted TEMPOs. The straightforward reaction gives a catalyst that has been tested in the oxidation of alcohols to aldehydes and ketones and gives reaction rates similar to TEMPOs when considered on a per nitroxyl basis. However, the new system gives an ∼ 3-fold higher primary over secondary selectivity. This reaction shows promise as a versatile method in the potential to synthesize rationally designed electroactive materials with a high biobased content.