Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of

2013, Volume 7, Issue 2

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Frontiers of Chemical Science and Engineering >> 2013, Volume 7, Issue 2 doi: 10.1007/s11705-013-1321-x

Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of

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

Available online: 2013-06-05

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Abstract

A facile method for the carbonylative cyclization of -bromobenzoic acid with primary amine using Pd(OAC) 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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