Synthesis 2016; 48(19): 3420-3428
DOI: 10.1055/s-0035-1562786
paper
© Georg Thieme Verlag Stuttgart · New York

Low-Temperature Intermolecular Addition of RCF2Li Compounds to Various Carbonyl Electrophiles for a Practical Synthesis of CF2-Containing Building Blocks

Mélanie Decostanzi
Institut Charles Gerhardt UMR 52 53 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: eric.leclerc@enscm.fr
,
Jean-Marc Campagne
Institut Charles Gerhardt UMR 52 53 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: eric.leclerc@enscm.fr
,
Eric Leclerc*
Institut Charles Gerhardt UMR 52 53 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France   Email: eric.leclerc@enscm.fr
› Author Affiliations
Further Information

Publication History

Received: 06 June 2016

Accepted after revision: 05 July 2016

Publication Date:
24 August 2016 (online)


This article is dedicated to the memory of Prof. Jean F. Normant and in tribute to his outstanding contribution to the field of organometallic chemistry.

Abstract

The addition of various RCF2Li compounds to a wide range of carbonyl electrophiles (aldehydes, ketones, acylsilanes, esters, and lactones) is reported. The reaction proceeds at very low temperature under Barbier conditions through a Br/Li exchange from the corresponding RCF2Br compounds. In contrast with existing methods that use more stable, but less reactive, organometallic species, there is efficient addition to esters, lactones and poorly reactive ketones.

Supporting Information

 
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