Tetrahedron

A free radical Mannich type reaction: Selective α-CH aminomethylation of ethers by Ti (III)/t-BuOOH system under aqueous acidic conditions

A Clerici, R Cannella, N Pastori, W Panzeri, O Porta

Index: Clerici, Angelo; Cannella, Rosalba; Pastori, Nadia; Panzeri, Walter; Porta, Ombretta Tetrahedron, 2006 , vol. 62, # 25 p. 5986 - 5994

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Citation Number: 33

Abstract

tert-Butoxy radical, generated by Ti (III)-one electron reduction of tert-butylhydroperoxide, selectively abstracts an α-H atom from ethers. The resulting α-ethereal radicals add to the C- atom of methylene iminium salts, formed in situ under aqueous acidic conditions, leading to a one-pot aminomethylation of ethers at room temperature. The aminoalkylation of ethers is also considered and the role of the metal ion is discussed.