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.


MS Metabolomics Laboratory, Instrumentation Center, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok Krt. 2., H-1117 Budapest, Hungary. [Email]


An efficient and practical method was developed for the synthesis of new (1,2,3triazol4yl)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 (1benzyl-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.


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