Potassium (1-Organo-1H-1,2,3-triazol-4-yl)trifluoroborates from ethynyltrifluoroborate through a regioselective one-pot Cu-catalyzed azide-alkyne cycloaddition reaction

摘要

A novel series of 1,4-disubstituted 1,2,3-triazole-containing potassium trifluoroborates were prepared in good to excellent yields from the corresponding organohalides and potassium ethynyltrifluoroborate through a regioselective one-pot Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Further Suzuki-Miyaura cross-coupling of these (organo-1,2,3-triazol-4-yl) trifluoroborates with aryl and alkenyl bromides by using a PdCl _2(dppf)·CH_2Cl_2/TBAB [dppf = 1,1′-bis(diphenylphosphanyl)ferrocene, TBAB = tetrabutylammonium bromide] system under microwave irradiation was explored. The preparation of potassium (1-organo-1H-1,2,3-triazol-4-yl)trifluoroborates from potassium ethynyltrifluoroborate and alkyl or aryl halides by employing a regioselective one-pot Cu-catalyzed azide-alkyne cycloaddition (CuAAC) is elaborated. This strategy allows unrestricted access to an infinite variety of 1,4-disubstituted 1,2,3-triazoles.