Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 24, Pages 15926-15947Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02398
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Funding
- European Research Council (ERC) [639170]
- ANR LabEx Chemistry of Complex Systems [ANR-10-LABX-0026 CSC]
- Region Grand -Est
- French Ministry of Higher Education
- China Scholarship Council
- European Research Council (ERC) [639170] Funding Source: European Research Council (ERC)
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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-1-Hindenes. 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 Bronsted 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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