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

doi:10.1055/s-2008-1032124

PAPER

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

Mhamed Lemhadri^a, Ahmed Battace^a, Florian Berthiol^a, Touriya Zair^b, Henri Doucet*^c, Maurice Santelli*^a
^a 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
Fax: +33(4)91983865; e-Mail: m.santelli@univ-cezanne.fr;
^b Laboratoire de Chimie Organique Appliquée, Faculté des Sciences, Université Moulay Ismail, BP 4010, Beni M’mhammed, 50000 Meknes, Morocco
^c Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-, Université de Rennes ‘Catalyse et Organometalliques’, Campus de Beaulieu, 35042 Rennes, France
Fax: +33(2)23236939; e-Mail: henri.doucet@univ-rennes1.fr;

Abstract

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Abstract

A wide variety of 1,3-dienes have been prepared by the Heck vinylation of vinyl bromides using [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 functionalised alkenes such as acrylates, enones, styrenes or a vinyl sulfone, and also with nonfunctionalised alkenes such as dec-1-ene, leading stereoselectively, in most cases, to the corresponding E- or E,E-1,3-dienes in good yields. Furthermore, this catalyst can be used at low loading for several reactions.

Key words

catalysis - palladium - tetraphosphine - alkenes - vinyl bromides

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