The Journal of Organic Chemistry

Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines

RJ Perry, SR Turner

Index: Perry, Robert J.; Turner, S. Richard Journal of Organic Chemistry, 1991 , vol. 56, # 23 p. 6573 - 6579

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Citation Number: 52

Abstract

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 OC, 90 psi of CO, 3% PdC12L2, and 2.4 equiv of DBU. This process is tolerant of a wide variety of functional groups and gives good yields of the ...