RESEARCH ARTICLE

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

  • Mayur V. KHEDKAR ,
  • Bhalchandra M. BHANAGE
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  • Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai 400019, India

Received date: 11 Dec 2012

Accepted date: 22 Jan 2013

Published date: 05 Jun 2013

Copyright

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg

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.

Cite this article

Mayur V. KHEDKAR , Bhalchandra M. BHANAGE . Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines[J]. Frontiers of Chemical Science and Engineering, 2013 , 7(2) : 226 -232 . DOI: 10.1007/s11705-013-1321-x

Acknowledgements

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