Skip to Main content Skip to Navigation
Journal articles

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
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.
Keywords : Hydrocarbons Anions Reaction products Stereoselectivity Molecular structure
Document type :
Journal articles
Complete list of metadatas
https://hal-normandie-univ.archives-ouvertes.fr/hal-02877369
Contributor : Madeleine Roux-Merlin <>
Submitted on : Monday, June 22, 2020 - 12:06:56 PM
Last modification on : Thursday, July 2, 2020 - 3:29:20 AM

Identifiers

Collections

COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | CNRS | ENSICAEN | UNILEHAVRE | UNICAEN

Citation

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

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

20