N-Halogeno compounds. Part 13. N-Fluoroquinuclidinium salts - synthesis and use as electrophilic fluorinating agents

Article abstract of DOI:10.1016/S0022-1139(00)80123-2

A convenient one-pot method has been developed for the preparation of the easily handled electrophilic fluorinating agent N-fluoroquinuclidinium triflate from quinuclidine, lithium triflate and fluorine.The corresponding trifluoroacetate, heptafluoro-n-butyrate and tetrafluoroborate salts were procured in a two-step fashion by adding the appropriate sodium salts to acetonitrile solutions of N-fluoroquinuclidinium fluoride.Site-specific fluorination of phenylmagnesium bromide (to PhF), diethyl sodio(phenyl)malonate , 2-nitropropan-2-yl-lithium , 1-morpholinocyclohexene >, phenol (to 2- and 4-FC6H4OH + 1,4-F2C6H3OH) and sodium benzenesulphinate (to PhSO2F) was achieved using these new N-fluoroquinuclidinium salts.