Benzylic oxidation of aromatics with cerium(IV) triflate; synthetic scope and mechanistic insight
Abstract
The synthetic utility of cerium(IV) triflate Ce(OTf)4
as a reagent for benzylic oxidation has been tested for a variety of aromatic
compounds. Insight is provided into various factors that govern these oxidations
and their progress. It has been shown that the mode of preparation of Ce(OTf
)4
and the % H2O present in the sample have a marked influence on
oxidation ability. A variety of mono- and dialkylbenzenes, haloalkylbenzenes,
bicyclic and tricyclic ring systems, and alkoxybenzenes have been surveyed.
The method offers an easy to perform one-pot reaction for the room temperature
synthesis of aromatic ketones and aldehydes from aromatics and has the potential
to find wider application.