A DABCO Derived Ionic Liquid Based on Tetrafluoroborate Anion: Preparation, Characterization and Evaluation of its Catalytic Activity in the Synthesis of 14-Aryl-14H-dibenzo[a, j]xanthenes

Abstract

A room-temperature ionic liquid (RTIL) derived from 1,4-diazabicyclo[2.2.2]octane (DABCO) consisting of tetrafluoroborate anion, 1-butyl-4-(4-sulfonylbutyl)-1,4-diazoniabicyclo[2.2.2]octane hydrogen sulfate tetrafluoroborate (<TEX>$[C_4DABCOC_4SO_3H][BF_4][HSO_4]$</TEX>) was synthesized and catalytically evaluated in the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes by cyclocondensation reaction of <TEX>${\beta}$</TEX>-naphthol and aryl aldehydes. This novel RTIL with an acidic <TEX>$SO_3H$</TEX> group showed high catalytic activity with good to excellent yields of the desired products in short reaction times. Moreover, the catalyst could be recovered and reused at least three times with only slight reduction in its catalytic activity.