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Catalytic Synthesis of Trifluoromethylated Allenes, Indenes, Chromenes, and Olefins from Propargylic Alcohols in HFIP

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journal contribution
posted on 2019-12-04, 17:39 authored by Florent Noël, Vuk D. Vuković, Jing Yi, Edward Richmond, Pavle Kravljanac, Joseph Moran
A general method to access CF3-substituted allenes from propargylic alcohols under Lewis acid catalysis in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvent is described. By tuning the reaction time and temperature, the obtained allenes rearrange to 1,3-biaryl-1-trifluoromethyl-1H-indenes. By tuning the structure of the propargylic alcohol substrates, a range of trifluoromethylated 2H-chromenes were successfully synthesized with the use of catalytic quantities of strong Brønsted acid in HFIP. The present method is therefore highly potent for the synthesis of a number of potentially pharmaceutically interesting new trifluoromethylated compounds and produces water as the only stoichiometric byproduct.

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