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

doi:10.1055/s-2006-950244

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Synthesis 2006(20): 3495-3505
DOI: 10.1055/s-2006-950244

PAPER

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^a, Touriya Zair^b, Henri Doucet*^a, Maurice Santelli*^a
^a 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
Fax: +33(4)91983865; e-Mail: henri.doucet@univ-cezanne.fr; 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

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Publication History

Received 7 June 2006
Publication Date:
10 October 2006 (online)

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Abstract

The adverse impact of sulfur compounds on catalytic performance is well known. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino)methyl]cyclopentane in combination with allylchloropalladium dimer affords an efficient catalyst 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. Using vinyl sulfides with 1 mol% catalyst, low to moderate yields of arylated alkenes were obtained. Phenyl vinyl sulfoxide was found to be more reactive, and satisfactory yields of (E)-[2-(phenylsulfinyl)vinyl]benzene derivatives were obtained using 1 mol% catalyst. With methyl vinyl sulfone, very high yields of (E)-[2-(methylsulfonyl)vinyl]benzene derivatives were obtained using 1-0.1 mol% catalyst. Phenyl vinyl sulfone and phenyl vinylsulfonate also gave high yields of the expected products, but in the presence of 0.4-1 mol% catalyst.

Key words

Heck reaction - palladium - phosphine - vinylsulfur - catalyst

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