Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes

Pauline Poutrel (1) , Xavier Pannecoucke (1) , Philippe Jubault (1) , Thomas Poisson (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Herein we report the hydrodefluorination reaction of trifluoromethylated alkenes to access terminal monofluoroalkenes. The use of LiAlH4 allowed the stereoselective synthesis of the terminal monofluoroalkenes in good to excellent yields with good to excellent diastereoselectivities. Mechanistic studies suggested a hydroalumination reaction followed by a stereoselective fluoride elimination.

Keywords: Hydrocarbons; Anions; Reaction products; Stereoselectivity; Molecular structure

Domains: Chemical Sciences

Pauline Poutrel, Xavier Pannecoucke, Philippe Jubault, Thomas Poisson. Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes. Organic Letters, 2020, 22 (12), pp.4858-4863. ⟨10.1021/acs.orglett.0c01701⟩. ⟨hal-02877369⟩