Regiodivergent Late-Stage Pd- or Ru-Catalyzed C-H Bond Functionalization Applied to the Straightforward Synthesis ofN-Methylated Diflufenican Derivatives

The late-stage C-H diversification methodology was applied to the preparation of arylated Diflufenican derivatives. Using a palladium catalyst associated with potassium pivalate, a regioselective arylation of the C-H bond flanked by the two fluorine atoms was observed. The reaction tolerated a wide range of useful functional groups on the aryl bromide. Conversely, the use of a ruthenium catalyst allowed to arylate the trifluoromethylbenzene ring of Diflufenican. To the best of our knowledge, these synthetic schemes are the first ones allowing the preparation of such arylated Diflufenican derivatives.