Add time:07/14/2019         Source:sciencedirect.com

Fluorine smoothly attacks quinuclidine-trifluoroborane, quinuclidine-pentafluorophosphorane, and quinuclidine-sulfur trioxide in acetonitrile at −35 °C to give the corresponding N-fluoroquinuclidinium salts NFQ+X− (X−  BF4−, PF6−, and FSO3− respectively; Q = quinuclidine). Like its tetrafluoroborate analogue (NFQ+BF4−), the hexafluorophosphate NFQ+PF6− can also prepared by direct fluorination of quinuclidine in the presence of the appropriate sodium salt (NaPF6). An alternative route to the tetrafluoroborate involves treatment of NFQ+F− with boron trifluoride. A comparative study of site-specific electrophilic fluorination of methoxybenzene [ → 1-fluoro-2- and 4-methoxybenzene], 2-hydroxynaphthalene ( → 1-fluoro-2-hydroxynaphthalene and 1,1-difluoro-2-oxo-1,2-dihydronaphthalene), 2-nitropropan-2-yl-lithium ( → 2-fluoro-2-nitropropane) and diethyl sodio(phenyl)malonate [ → diethyl fluoro(phenyl)malonate] with all of the NFQ+X− salts mentioned above, plus the triflate (X−  CF3SO3−), revealed that the hexafluorophosphate and triflate are the most easily-handled and effective reagents.

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