Tetrahedron letters

TiCl 3/PhN 2+-mediated radical addition of ethers to aldimines generated in situ under aqueous conditions

A Clerici, R Cannella, W Panzeri, N Pastori, E Regolini…

Index: Cannella, Rosalba; Clerici, Angelo; Pastori, Nadia; Regolini, Eva; Porta, Ombretta Organic Letters, 2005 , vol. 7, # 4 p. 645 - 648

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Citation Number: 11

Abstract

Ti (III)-mediated one-electron reduction of phenyldiazonium cation, followed by phenyl radical α-H atom abstraction from ethers, leads to one-pot radical addition of ethers to the C- atom of imines generated in situ from the corresponding aldehydes and imines under aqueous conditions. The reaction is not limited to aromatic aldehydes and may be applied to imines generated in situ from formaldehyde and enolizable aldehydes.