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

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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.

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Authors and Affiliations

  1. Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai, 400019, India

    Mayur V. Khedkar & Bhalchandra M. Bhanage

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  1. Mayur V. Khedkar
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  2. Bhalchandra M. Bhanage
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Correspondence to Bhalchandra M. Bhanage.

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Khedkar, M.V., Bhanage, B.M. Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines. Front. Chem. Sci. Eng. 7, 226–232 (2013). https://doi.org/10.1007/s11705-013-1321-x

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  • DOI: https://doi.org/10.1007/s11705-013-1321-x

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