Synthesis of Phthalide Derivatives Using Nickel??Catalyzed Cyclization of o??Haloesters with Aldehydes

DK Rayabarapu, HT Chang…

Index: Rayabarapu, Dinesh Kumar; Chang, Hong-Tai; Cheng, Chien-Hong Chemistry - A European Journal, 2004 , vol. 10, # 12 p. 2991 - 2996

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Citation Number: 25

Abstract

Abstract The reaction of o-bromobenzoate (1 b) with benzaldehyde (2 a) in the presence of [NiBr 2 (dppe)](dppe= 1, 2-bis (diphenylphosphino) ethane) and zinc powder in THF (24 hours, reflux temperature), afforded 3-phenyl-3H-isobenzofuran-1-one (3 a) in an 86% yield. Similarly, o-iodobenzoate reacts with 2 a to give 3 a, but in a lower yield (50%). A series of substituted aromatic and aliphatic aldehydes (2 b, 4-MeC 6 H 4 CHO; 2 c, 4-MeOC 6 H 4 ...