Synthesis 2002(4): 0543-0551
DOI: 10.1055/s-2002-20971
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalysed Cross-Coupling of Iodovinylic Acids with Organometallic Reagents. Selective Synthesis of 3,3-Disubstituted Prop-2-enoic Acids

Mohamed Abarbria, Jérôme Thibonneta, Jean-Luc Parrainb, Alain Duchêne*a
a Laboratoire de Physicochimie des Interfaces et des Milieux Réactionnels, Faculté des Sciences de Tours, Parc de Grandmont, 37200 Tours, France
Fax: +33(2)47366960; e-Mail: duchene@delphi.phys.univ-tours.fr;
b Laboratoire de Synthèse Organique UMR 6009 CNRS, Case postale D120, Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, F.13397 Marseille Cedex 20, France
Fax: +33(4)91983865; e-Mail: jl.parrain@lso.u-3mrs.fr;
Further Information

Publication History

Received 9 December 2001
Publication Date:
28 July 2004 (online)

Abstract

3,3-Disubstituted prop-2-enoic acids were selectively prepared in good yields under mild experimental conditions via palladium-catalysed cross-coupling of 3-substituted 3-iodobut-2-enoic acids with miscellaneous organometallic reagents using dichlorobis(acetonitrile)palladium(II) as catalyst and DMF as solvent.

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We found that these attempts required a higher temperature and removal of the excess acetic acid used was difficult.