Issue 2, 2003
From the journal:

New Journal of Chemistry

Efficient preparation of β-trifluoromethyl acrylates and derivatives via palladium cross-coupling reactions

Gildas Prié,a   Mohamed Abarbri,a   Jérôme Thibonnet,ab   Jean-Luc Parrainb  and  Alain Duchêne*a  

* Corresponding authors

a Laboratoire de Physicochimie des Interfaces et des Milieux Réactionnels (CNRS EA 2098-LRC-MO2), Faculté des Sciences de Tours, Parc de Grandmont, Tours, France
E-mail: duchene@delphi.phys.univ-tours.fr
Fax: +33 (0)2 47 36 70 40
Tel: +33 (0)2 47 36 69 59

b Laboratoire de Synthèse Organique associé au CNRS, Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, Marseille cedex 20, France
E-mail: jl.parrain@univ.u-3mrs.fr
Fax: +33 (0)4 91 98 38 65
Tel: +33 (0)4 91 28 89 14

Abstract

Stereoselective construction of 3-trifluoromethyl conjugated dienoates, trienoates or dienynoates was achieved from ethyl (Z)-4,4,4-trifluoro-3-iodobutenoate and alkenyltin or alkynyltin reagents through the Stille reaction or under Heck–Sonogashira coupling conditions. Reduction of ethyl 3-trifluoromethyldienoates using DIBAL-H selectively yielded allylic alcohols and hydrolysis with lithium hydroxide yielded the corresponding acids.

Graphical abstract: Efficient preparation of β-trifluoromethyl acrylates and derivatives via palladium cross-coupling reactions

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Article information

DOI
https://doi.org/10.1039/B207648A
Article type
Paper
Submitted
31 Jul 2002
Accepted
28 Oct 2002
First published
03 Jan 2003

New J. Chem., 2003,27, 432-441

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Efficient preparation of β-trifluoromethyl acrylates and derivatives via palladium cross-coupling reactions

G. Prié, M. Abarbri, J. Thibonnet, J. Parrain and A. Duchêne, New J. Chem., 2003, 27, 432 DOI: 10.1039/B207648A

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