Pd- and Cu-catalyzed stereo- and regiocontrolled decarboxylative/C-H fluoroalkenylation of heteroarenes

Kevin Rousée; Cédric Schneider; Samuel Couve-Bonnaire; Xavier Pannecoucke; Vincent Levacher; Christophe Hoarau

doi:10.1002/chem.201405119

Pd- and Cu-catalyzed stereo- and regiocontrolled decarboxylative/C-H fluoroalkenylation of heteroarenes

Chemistry. 2014 Nov 10;20(46):15000-4. doi: 10.1002/chem.201405119. Epub 2014 Oct 9.

Authors

Kevin Rousée¹, Cédric Schneider, Samuel Couve-Bonnaire, Xavier Pannecoucke, Vincent Levacher, Christophe Hoarau

Affiliation

¹ Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière 76821 Mont-Saint-Aignan Cedex (France).

PMID: 25303004
DOI: 10.1002/chem.201405119

Abstract

Pd/Cu-catalyzed decarboxylative/direct C-H alkenylations of heteroarenes with α-fluoroacrylic acid is reported. This method offers step-economical and stereocontrolled access to valuable heteroarylated monofluoroalkenes as both Z and E isomers, which are known to be useful in the synthesis of fluorinated biomolecules.

Keywords: CH activation; alkenylation; decarboxylation; fluoroalkenes; heterocycles; palladium.