Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes

Pauline Poutrel, Xavier Pannecoucke, Philippe Jubault* and Thomas Poisson*

*Normandie Université, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France, Email: philippe.jubaultinsa-rouen.fr, thomas.poissoninsa-rouen.fr

P. Poutrel, X. Pannecoucke, P. Jubault, T. Poisson, Org. Lett., 2020, 22, 4858-4863.

DOI: 10.1021/acs.orglett.0c01701

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Abstract

A stereoselectiv hydrodefluorination reaction of trifluoromethylated alkenes with LiAlH₄ provides terminal monofluoroalkenes in very good yields and diastereoselectivities. Mechanistic studies suggested a hydroalumination reaction followed by a stereoselective fluoride elimination.

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Key Words

alkenyl halides, alkenyl fluorides, lithium aluminum hydride

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ID: J54-Y2020