Efficient Synthesis of Substituted Styrenes and Biaryls (or Heteroaryls) with Regioselective Reactions of ortho-, meta-, and para-Bromobenzyl Bromide

Elsa Anselmi; Mohamed Abarbri; Alain Duchêne; Sandrine Langle-Lamandé; Jérôme Thibonnet

doi:10.1055/s-0031-1290987

Synthesis, Table of Contents

Synthesis 2012; 44(13): 2023-2040
DOI: 10.1055/s-0031-1290987

paper

Efficient Synthesis of Substituted Styrenes and Biaryls (or Heteroaryls) with Regioselective Reactions of ortho-, meta-, and para-Bromobenzyl Bromide

Elsa Anselmi

^aLaboratoire d’Infectiologie et Santé Publique (UMR UFR/INRA 1282), Equipe ‘Recherche et Innovation en Chimie Médicinale’ Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France, Email: jerome.thibonnet@univ-tours.fr

,

Mohamed Abarbri

^aLaboratoire d’Infectiologie et Santé Publique (UMR UFR/INRA 1282), Equipe ‘Recherche et Innovation en Chimie Médicinale’ Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France, Email: jerome.thibonnet@univ-tours.fr

,

Alain Duchêne

^aLaboratoire d’Infectiologie et Santé Publique (UMR UFR/INRA 1282), Equipe ‘Recherche et Innovation en Chimie Médicinale’ Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France, Email: jerome.thibonnet@univ-tours.fr

,

Sandrine Langle-Lamandé*

^bGroupe S.U.C.R.E.S – UMR 7565 Nancy Université – CNRS, BP 70239, 54506 Nancy Vandoeuvre, France

,

Jérôme Thibonnet*

^aLaboratoire d’Infectiologie et Santé Publique (UMR UFR/INRA 1282), Equipe ‘Recherche et Innovation en Chimie Médicinale’ Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France, Email: jerome.thibonnet@univ-tours.fr

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Abstract

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Abstract

Regio- and stereoselective reactions of ortho-, meta-, and para-bromobenzyl bromide under Stille and (or) Suzuki cross-coupling reactions are described that provided substituted styrene monomers and biaryls in two steps. By controlling the experimental conditions, the first coupling provided access to allylarene or diarylmethane intermediates, and the second reaction led to the desired styrenes and biaryls, substituted by a spacer arm in the ortho, meta or para position depending on the starting material.

Key words

Stille reaction - palladium - regioselectivity - organometallic reagents - biaryls

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References

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