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

Tripolszky, Anna and Németh, Krisztina and Szabó, Pál Tamás and Bálint, Erika (2019) 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. MOLECULES, 24. No. 2085. ISSN 1420-3049

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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.

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