A method to prepare 5-iodo-1,2,3-triazole directly from organic azide and terminal alkyne mediated by in situ generated copper(I) and iodinating agents is reported. This work is an extension from our previous report (Brotherton, W. S. et al. J. Org. Chem. 2012 , 77, 6443-6455). The major methodological advance of the current procedure is to achieve high conversion and iodo/proto selectivity of a broad substrate scope without using an excess amount of alkyne, which was required in the previous method. The use of an accelerating ligand is key to the success of reactions involving unreactive azides or alkynes. New mechanistic insights are provided, including the confirmation of 1-iodoalkyne formation as a key intermediate step under the established conditions.

Synthesis of 5-iodo-1,2,3-triazole from organic azide and terminal alkyne: Ligand acceleration effect, substrate scope, and mechanistic insight

246th National Meeting (2013)

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