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.santelliuniv-cezanne.fr

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

DOI: 10.1055/s-2008-1032124

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Abstract

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

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Efficient Heck Vinylation of Aryl Halides Catalyzed by a New Air-Stable Palladium-Tetraphosphine Complex

M. Feuerstein, H. Doucet, M. Santelli, J. Org. Chem., 2001, 66, 5923-5925.

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.

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Key Words

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

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ID: J66-Y2008-0890