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

Chem Commun (Camb). 2023 Oct 26;59(86):12891-12894. doi: 10.1039/d3cc04126c.

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.