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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

Ahmed Battace, Touriya Zair, Henri Doucet*, Maurice Santelli*

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

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

DOI: 10.1055/s-2006-950244


Tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino)methyl]cyclopentane (Tedicyp) is an efficient ligand for the Heck reaction of sulfur-containing alkenes with aryl bromides. The rates and yields of the reactions strongly depend on the oxidation state of the sulfur atom.

see article for more examples

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.

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

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

Key Words

Heck Reaction, Vinyl Sulfones, Sulfoxides, Vinyl Sulfides

ID: J66-Y2006-3530