1 2 3 triazole

The 1,3-dimethyl-1,2,3-triazolium salts were synthesized by direct methylation of 1,2,3-Triazole or via the intermediate lithium 1,2,3-triazolate (see Figure 1). The detailed synthesis procedures and extensive characterization data of all the reported 1,2,3-triazolium salts can be found in the Supplementary Materials. 1,2,3-Triazole used for their syntheses was received from abcr GmbH (Karlsruhe, Germany). Methyl iodide, potassium carbonate, N-methyl bis((trifluoromethyl)sulfonyl)imide, and methyl triflate were purchased from Sigma-Aldrich/Merck (Darmstadt, Germany). Silver fluoride was received from Alfa Aesar (Haverhill, MA, USA). Tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), methylene chloride, and methanol were purchased from VWR (Radnor, PA, USA), Carl Roth (Karlsruhe, Germany), Overlack (Mönchengladbach, Germany), and Brenntag (Essen, Germany), respectively.

The compounds used for the synthesis, 1-ethyl-3-methylimidazolium chloride (>99%), methyl iodide (99.5%), potassium carbonate (≥99%), silver benzoate (99%), and sodium salicylate (≥99.5%), were received from Sigma Aldrich. Silver nitrate (≥99.5%) was purchased from Carl Roth. 1,2,3-Triazole (98%) and ethyl bromide (98%) were purchased from abcr GmbH. The solvents tetrahydrofuran (≥99.9%), dimethyl sulfoxide–d ${}_6$ (99.8 atom-% D), acetone (≥99.5%), chloroform–d ${}_1$ (99.8 atom-% D), and methanol (≥99%) were received from VWR, Armar Europa GmbH, Sigma Aldrich, and Carl Roth (water content below 100 ppm in all cases). Microcrystalline cellulose with a particle size of 20 $\mathsf{\mu }$ m and a molar mass of 37 kg mol ${}^{-1}$ (as determined by viscosimetry) was purchased from Sigma Aldrich.