Synthesis 2006(20): 3409-3418  
DOI: 10.1055/s-2006-950208
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Fluoroalkenes via Diethylzinc-Promoted Wittig Reaction

Ludivine Zoute, Guillaume Dutheuil, Jean-Charles Quirion, Philippe Jubault*, Xavier Pannecoucke*
IRCOF, LHO, UMR CNRS 6014, Université et INSA de Rouen, Rue Lucien Tesnière, 76131 Mont-Saint-Aignan, France
e-Mail: philippe.jubault@insa-rouen.fr; e-Mail: xavier.pannecoucke@insa-rouen.fr ;
Further Information

Publication History

Received 2 June 2006
Publication Date:
21 August 2006 (online)

Abstract

The synthesis of α-fluoroacrylates and α-bromo-α-fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in the addition sequence was critical in order to obtain exclusively α-fluoroacrylates in good yields.