Synthesis of 1,3-Dialkyl-1,2,3-triazolium Ionic Liquids and Their Applications to the Baylis-Hillman Reaction

Novel 1,3-dialkyl-1,2,3-triazolium ionic liquids were synthesized via click reactions using 1-trimethylsilylacetylene and alkyl azides and were efficient reaction media for the Baylis-Hillman reaction. The problems associated with deprotonation of the C-2 hydrogen of [bmim][PF(6)] could be suppressed in the reaction of [bmTr][PF(6)] or [bmTr][NTf(2)]. 1,3-Dialkyl-1,2,3-triazolium ionic liquids are chemically inert under basic conditions and more suitable media for the reactions involving bases than the common 1,3-dialkylimidazolium ionic liquids.