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

Mélanie Decostanzi; Jean-Marc Campagne; Eric Leclerc

doi:10.1055/s-0035-1562786

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(19): 3420-3428
DOI: 10.1055/s-0035-1562786

paper

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

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Abstract

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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.

Key words

fluorine - organolithium - carbenoid - acylsilanes - ketones - esters - lactones

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Referenzen

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