Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines

Abstract

A facile method for the carbonylative cyclization of o-bromobenzoic acid with primary amine using Pd(OAC)₂ as a metal precursor and 1,1'-bis(diphenylphosphino)ferrocene (dppf) as a ligand has been developed. The effect of various reaction parameters such as ligand, solvent, base, time and temperature on this cyclization was studied. The optimized protocol was used for a wide variety of substituted aryl amines with different steric and electronic properties, affording the corresponding isoindoline-1,3-diones in good to excellent yields under atmospheric pressure of carbon monoxide at 100°C within 10 h using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base. The reaction system finds attractive alternative to the conventional multistep synthetic process and thus represents an effective utilization of carbonylative protocol for synthesis of valuable chemicals.

Keywords

carbonylative cyclization reactions / isoindole-1,3-dinones / homogeneous catalysis / dppf

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Acknowledgements

The author (M. V. Khedkar) is greatly thankful to UGC (University Grant Commission, India) for providing Junior Research Fellowship.

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2014 Higher Education Press and Springer-Verlag Berlin Heidelberg