Ruthenium-catalysed C–H/C–N bond activation: facile access to isoindolinones

Abstract

A facile ruthenium-catalysed C–H/C–N bond activation and the subsequent annulation of readily available benzoic acids with in situ generated formaldimines are reported. The choice of solvent and base is critical for this reaction. This protocol allows the efficient synthesis of a wide range of biologically important isoindolinones in useful to excellent yields without the use of any external oxidants. The late-stage modification of bioactive acids such as adapalene, bexarotene and flufenamic acid demonstrated the synthetic utility of this methodology.