Synthesis of (1,2,3-triazol-4-yl)methyl Phosphinates and (1,2,3-Triazol-4-yl)methyl Phosphates by Copper-Catalyzed Azide-Alkyne Cycloaddition

Abstract

An efficient and practical method was developed for the synthesis of new (1,2,3‑triazol‑4‑yl)methyl phosphinates and (1,2,3-triazol-4-yl)methyl phosphates by the copper(I)‑catalyzed azide-alkyne cycloaddition (CuAAC) of organic azides and prop-2-ynyl phosphinate or prop-2-ynyl phosphate. The synthesis of (1‑benzyl-1H-1,2,3-triazol-4-yl)methyl diphenylphosphinate was optimized with respect to the reaction parameters, such as the temperature, reaction time, and catalyst loading. The approach was applied to a range of organic azides, which confirmed the wide scope and the substituent tolerance of the process. The method elaborated represents a novel approach for the synthesis of the target compounds.

Keywords

• 1,2,3-triazol
• triazolylmethyl phosphinate
• triazolylmethyl phosphate
• copper-catalyzed azide-alkyne cycloaddition
• click reaction