Article ID Journal Published Year Pages File Type
5280273 Tetrahedron Letters 2005 4 Pages PDF
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 and promoters and the use of 'radical clocks' indicate a stepwise reaction mechanism initiated by the attack of an alkyl radical to iminium ion.

Graphical abstractZinc in protic medium promotes aminomethylation of organic halides via a radical process.Download full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
Authors
, , ,