Benzylic oxidation of aromatics with cerium(IV) triflate; synthetic scope and mechanistic insight

The synthetic utility of cerium(IV) triflate Ce(OTf)(4) as a reagent for be nzylic oxidation has been tested for a variety of aromatic compounds. Insig ht 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 abilit y. A variety of mono- and dialkylbenzenes, haloalkylbenzenes, bicyclic and tricyclic ring systems, and alkoxybenzenes have been surveyed. The method o ffers an easy to perform one-pot reaction for the room temperature synthesi s of aromatic ketones and aldehydes from aromatics and has the potential to find wider application.