Synthesis 2015; 47(11): 1534-1546
DOI: 10.1055/s-0034-1380548
short review
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fluorinated and Trifluoromethyl-Substituted Alkenes through the Modified Julia Olefination: An Update

Emmanuel Pfund
a  Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, FR3038, ENSICAEN, Université de Caen Basse-Normandie, 6 Bd. du Maréchal Juin, 14050 Caen Cedex, France   Email: thierry.lequeux@ensicaen.fr
,
Thierry Lequeux*
a  Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, FR3038, ENSICAEN, Université de Caen Basse-Normandie, 6 Bd. du Maréchal Juin, 14050 Caen Cedex, France   Email: thierry.lequeux@ensicaen.fr
,
David Gueyrard*
b  Laboratoire Chimie Organique 2 Glycochimie, Université de Lyon, ICBMS, UMR CNRS 5246, Bat. 308 – Curien (CPE Lyon), Université Claude Bernard Lyon 1, 43 Bd. du 11 Novembre 1918, 69622 Villeurbanne, France   Email: david.gueyrard@univ-lyon1.fr
› Author Affiliations
Further Information

Publication History

Received: 28 January 2015

Accepted after revision: 19 March 2015

Publication Date:
16 April 2015 (online)


Dedicated to Professor Patrick Rollin on the occasion of his 70th birthday.

Abstract

The modified Julia olefination is now a powerful tool for the synthesis of a large range of functionalized alkenes. This short review covers the last five years and provides an overview of the synthesis of mono-, difluoro-, and trifluoromethyl-substituted alkenes via the modified Julia olefination focusing on the novel scope of this reaction.

1 Introduction

2 Monofluoroalkenes

2.1 Disubstituted α- and β-Monofluoroalkenes

2.2 Bis(trifluoromethyl)phenyl Sulfones

2.3 Conjugated Monofluoroalkenes

2.4 Intramolecular Julia Olefination

2.5 Smiles Rearrangement from Fluorinated Keto Sulfones

2.6 Fluoroallylamines

2.7 Fluorinated exo-Glycals

2.8 Monofluoroalkenes with an α-Stereocenter at the Allylic Position

3 1,1-Difluoroalkenes

4 Trifluoromethyl-Substituted Alkenes

5 Conclusion

 
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