Organic letters

Efficient synthesis of 2-substituted-1, 2, 3-triazoles

J Kalisiak, KB Sharpless, VV Fokin

Index: Kalisiak, Jaroslaw; Sharpless, K. Barry; Fokin, Valery V. Organic Letters, 2008 , vol. 10, # 15 p. 3171 - 3174

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Citation Number: 119

Abstract

In this three-component reaction, alkynes undergo a copper (I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2 H-1, 2, 3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to NH-1, 2, 3- triazoles. The reaction is experimentally simple and readily scalable.