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

作　　者：Mayur V. KHEDKAR Bhalchandra M. BHANAGE 

机构地区：[1]Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai 400019, India

出　　处：《Frontiers of Chemical Science and Engineering》2013年第2期226-232,共7页化学科学与工程前沿（英文版）

摘　　要：A facile method for the carbonylative cycliza- tion of o-bromobenzoic acid with primary amine using Pd（OAC）2 as a metal precursor and 1, l′-bis（diphenylpho- sphino）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-l,3-diones in good to excellent yields under atmospheric pressure of carbon monoxide at 100℃ within 10h 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 repre- sents an effective utilization of carbonylative protocol for synthesis of valuable chemicals.A facile method for the carbonylative cycliza- tion of o-bromobenzoic acid with primary amine using Pd（OAC）2 as a metal precursor and 1, l′-bis（diphenylpho- sphino）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-l,3-diones in good to excellent yields under atmospheric pressure of carbon monoxide at 100℃ within 10h 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 repre- sents an effective utilization of carbonylative protocol for synthesis of valuable chemicals.

关 键 词：carbonylative cyclization reactions isoindole-1 3-dinones homogeneous catalysis DPPF 

分 类 号：TQ655[化学工程—精细化工] O614.33[理学—无机化学]