Aryl and alkyl β-heteroatom-trisubstituted vinyl triflones react
with THF and cyclohexane to undergo
trifluoromethyl radical-mediated C−H functionalization reactions to
afford E and Z β-heteroatom-trisubstituted
olefins.
Most reactions proceed with both high yield and high
stereospecificity (retention of configuration).
β-Substituents
which have been employed in this study are iodine, bromine, fluorine,
benzoate, ethylcarbonate, and phthalimide.
β-Substituents bearing powerful electron-releasing groups such
as alkoxy or amino render the vinyl triflone unreactive.
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