Synthesis 2006(9): 1542-1548  
DOI: 10.1055/s-2006-926432
PAPER
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalysed Reformatsky-Type Reactions

Muriel Durandetti*, Jacques Périchon
Laboratoire d’Electrochimie, Catalyse et Synthèse Organique, UMR 7582, CNRS-Université Paris, 12 Val de Marne, 2 rue Henri-Dunant, 94320 Thiais, France
Fax: +33(2)35522971; e-Mail: muriel.durandetti@univ-rouen.fr;
Further Information

Publication History

Received 6 December 2005
Publication Date:
11 April 2006 (eFirst)

Abstract

A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloroesters or nitriles can both be converted into their corresponding derivatives. The method was applicable to both ketones and aldehydes, resulting in the formation of β-hydroxyesters under mild conditions.

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New address: Dr. M. Durandetti, Laboratoire des Fonctions Azotées & Oxygénées Complexes de L’IRCOF, UMR 6014 CNRS, Université de Rouen, 76821 Mont Saint-Aignan Cedex, France.