A Selective Approach to Pyridine Appended 1,2,3-Triazolium Salts

A selective and highly efficient strategy to obtain a library of pyridine appended 1,4-disubstituted-3-methyl-1,2,3-triazolium salts is described. It features pyridine nitrogen protection at click-derived pyridyl-triazoles through N-oxidation with subsequent N3 alkylation of the triazole ring and deprotection. Triazolium salts are obtained in high yield and purity in either a stepwise or one-pot protocol. Preliminary data indicate their remarkable efficiency in palladium-catalyzed Suzuki-Miyaura catalysis in the environmentally benign solvent water.