Thermal, non-catalyzed Huisgen cycloaddition for the preparation of 4,5-bis(trimethylsilyl)-1H-1,2,3-triazoles

The 1,2,3-triazole scaffold is an important pharmacophore and a versatile, increasingly leveraged, substructure in biochemical, materials, polymer, and metal-coordinating applications. Continuing advances in 1,2,3-triazole construction, by either non-catalyzed or metal-catalyzed azide/alkyne cycloaddition, foster further creative use. The work reported here establishes a general protocol for the synthesis of 4,5-bis(trimethylsilyl)-1H-1,2,3-triazoles via thermal Huisgen cycloaddition between azides and bis(trimethylsilyl)acetylene.