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Palladium-Tetraphosphine Complex Catalysed Heck Reaction of Vinyl Bromides with Alkenes: A Powerful Access to Conjugated Dienes

Mhamed Lemhadri, Ahmed Battace, Florian Berthiol, Touriya Zair, Henri Doucet, Maurice Santelli*

*Laboratoire de Synthèse Organique, Faculté des Sciences de Saint Jérôme, UMR 6180 CNRS, Université d'Aix-Marseille III, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France, Email:

M. Lemhadri, A. Battace, F. Berthiol, T. Zair, H. Doucet, M. Santelli, Synthesis, 2008, 1142-1152.

DOI: 10.1055/s-2008-1032124


A broad range of 1,3-dienes have been prepared by the Heck olefination of vinyl bromides using low loadings of [Pd(η3-C3H5)Cl]2/cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino)methyl]cyclopentane (Tedicyp) as the catalyst precursor. Both α- and β-substituted vinyl bromides undergo the Heck reaction with nonfunctionalised and functionalised alkenes such as acrylates, enones, styrenes.

see article for more examples

Heck Vinylations Using Vinyl Sulfide, Vinyl Sulfoxide, Vinyl Sulfone, or Vinyl Sulfonate Derivatives and Aryl Bromides Catalyzed by a Palladium Complex Derived from a Tetraphosphine

A. Battace, T. Zair, H. Doucet, M. Santelli, Synthesis, 2006, 3495-3505.

Key Words

catalysis, palladium, tetraphosphine, alkenes, vinyl bromides, 1,3-dienes, Heck Reaction

ID: J66-Y2008-0890