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

Facile synthesis of isoindoline-l,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines
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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.
出处 《Frontiers of Chemical Science and Engineering》 SCIE EI CAS CSCD 2013年第2期226-232,共7页 化学科学与工程前沿(英文版)
关键词 carbonylative cyclization reactions isoindole-1 3-dinones homogeneous catalysis DPPF carbonylative cyclization reactions, isoindole-1,3-dinones, homogeneous catalysis, dppf
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