Mechanochemical Synthesis of Tripodal Tris[4-(1,2,3-triazol-5-ylidene)methyl]amine Mesoionic Carbene Ligands and Their Complexation with Silver(I).

The conjugate acids of 1,2,3-triazolylidene mesoionic carbenes can be prepared in a straightforward fashion by alkylation of 1-substituted 1,2,3-triazoles. However, this becomes a much more challenging proposition when other nucleophilic centers are present, which has curtailed the development of ligands containing multiple 1,2,3-triazolylidene donors. Herein, methylation of a series of tris[(1-aryl-1,2,3-triazol-4-yl)methyl]amines possessing both electron-rich and electron-deficient aromatic substituents, using MeOBF, is shown to proceed with much higher chemoselectivity under mechanochemical conditions than when conducted in solution.