alpha- and beta-Stannyl Trifluoromethylbutenoates: Regioselective Preparation and Use in Copper(I)-Catalyzed Allylation and Propargylation Reactions - Aix-Marseille Université Access content directly
Journal Articles Advanced Synthesis and Catalysis Year : 2010

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

Abstract

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.

Dates and versions

hal-00679276 , version 1 (15-03-2012)

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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⟩
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