alpha- and beta-Stannyl Trifluoromethylbutenoates: Regioselective Preparation and Use in Copper(I)-Catalyzed Allylation and Propargylation Reactions

Yvan Carcenac (1) , Khalid Zine (1) , Jean-Claude Kizirian (1) , Jérôme Thibonnet (1) , Alain Duchêne (1) , Jean-Luc Parrain (2) , Mohamed Abarbri (1)

1 PCMB - EA4244 - Laboratoire Physicochimie des matériaux et des biomolécules
2 STeRéO

The palladium-free hydrostannylation of ethyl 4,4,4-trifluorobutynoate with tributyltin hydride at room temperature is highly regio- and stereoselective, providing good yields of beta-trifluoro- methyl (Z)-alpha- or (Z)-beta-stannylacrylates. Vinyl- stannanes undergo a copper(I)-catalyzed coupling reactions with allylic or propargylic bromides leading selectively to good yields of the corresponding allylated or propargylated products without allylic or allenic transposition.

Mots clés: allylation; copper(I)-catalyzed cross coupling; ethyl trifluorobutynoate; propargylation; regioselective; hydrostannylation

Domaines: Chimie organique

Yvan Carcenac, Khalid Zine, Jean-Claude Kizirian, Jérôme Thibonnet, Alain Duchêne, et al.. alpha- and beta-Stannyl Trifluoromethylbutenoates: Regioselective Preparation and Use in Copper(I)-Catalyzed Allylation and Propargylation Reactions. Advanced Synthesis and Catalysis, 2010, 352, pp.949-954. ⟨10.1002/adsc.200900828⟩. ⟨hal-00679276⟩