1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) as novel and versatile reagent for the rapid thiocyanation of indoles, azaindole, and carbazole

Selectfluor (TM) is found to catalyze efficiently the electrophilic thiocyanation of indoles and pyrrole with ammonium thiocyanate under mild and neutral conditions to produce the corresponding 3-indolyl and 2-pyrrolyl thiocyanates, respectively, in excellent yields with high selectivity. This method is effective even with azaindole and carbazole while many of reported procedures failed to produce thiocyanates from azaindole.