Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes - Normandie Université Access content directly
Journal Articles Organic Letters Year : 2020

Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes

Abstract

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.
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hal-02877369 , version 1 (22-06-2020)

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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⟩
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