Direct synthesis of phthalimides via palladium-catalysed double carbonylation of o-dihaloarenes with nitroarenes

Abstract

The direct carbonylation of readily available nitro compounds is more attractive and straightforward than the use of traditional amines as nucleophiles. Herein, a practical palladium-catalysed double carbonylation of nitroarenes with o-dihaloarenes has been developed for the construction of various N-aryl phthalimides. Key to the success of this transformation is the use of Mo(CO)₆, which acts as both a reducing agent and a solid carbonyl source. A wide range of nitroarenes and o-dihaloarenes as well as o-iodobenzoic acids reacted smoothly to give phthalimides in 27–94% yields.