Aminomethylation of organic halides promoted by zinc in protic medium

IHS Estevam, MF da Silva, LW Bieber

Index: Estevam, Idalia H. S.; Da Silva, Margarete F.; Bieber, Lothar W. Tetrahedron Letters, 2005 , vol. 46, # 44 p. 7601 - 7604

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Citation Number: 7

Abstract

Organic halides undergo smooth aminomethylation by secondary amines and aqueous formaldehyde promoted by metallic zinc under copper (I) catalysis. Good to excellent yields are obtained with primary, secondary, and tertiary iodides, allylic, propargylic, and benzylic bromides and with α-bromoesters. In most cases, DMSO is the best solvent, but dioxane is preferable for some more reactive halides. Additional experiments with radical quenchers ...