The oxidation of alcohols with trichloroisocyanuric acid: pyridine from base to organocatalyst

Abstract

An alcohol oxidation method based on the use of pyridine or 3-cyanopyridine as an organocatalyst in combination with trichloroisocyanuric acid as the terminal oxidant is reported. It is demonstrated that secondary aliphatic alcohols can be selectively oxidized to the corresponding ketones in the presence of primary aliphatic alcohols. The method is also suitable for the oxidation of primary and secondary benzylic alcohols. N-Chloropyridinium cyanurates are proposed as the active alcohol-oxidizing species.