PREPARATION OF N-SUBSTITUTED PHTHALIMIDES BY THE PALLADIUM-CATALYZED CARBONYLATION AND COUPLING OF ORTHO-DIHALO AROMATICS AND PRIMARY AMINES
PREPARATION OF N-SUBSTITUTED PHTHALIMIDES BY THE PALLADIUM-CATALYZED CARBONYLATION AND COUPLING OF ORTHO-DIHALO AROMATICS AND PRIMARY AMINES
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DOI：
10.1021/jo00023a023
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发表时间：
1991-11-08
影响因子：
3.6
通讯作者：
TURNER, SR
中科院分区：
文献类型：
--
作者：
PERRY, RJ;TURNER, SR
描述了一种形成 N-取代邻苯二甲酰亚胺的新方法，该方法基于钯催化的羰基化以及邻二卤代芳烃和伯胺的偶联。 使用邻二碘苯和苯胺进行反应的最佳条件为 DMAc (0.2 M)、115 摄氏度、90 psi CO、3% PdCl2L2 和 2.4 当量 DBU。 该方法能够耐受多种官能团，并能获得良好的所需产物收率。 检查温度、催化剂类型和负载、CO 压力、溶剂和碱等变量以优化该反应。 苯胺与1,2-二溴环戊烯在相似条件下反应得到多种产物。
A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115-degrees-C, 90 psi of CO, 3% PdCl2L2, and 2.4 equiv of DBU. This process is tolerant of a wide variety of functional groups and gives good yields of the desired products. Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction. The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.