The copper-catalyzed azide-alkyne cycloaddition reaction (“CuAAC” or “click” reaction) is a reaction well known for its high efficiency and broad applicability in many disciplines. This reaction joins together a terminal alkyne and an organic azide to give exclusively 1,4-disubstituted-1,2,3-triazoles in excellent yield and has been subject to intensive mechanistic study. Hein, Fokin, and co-workers reported the regiospecific Cu(I)-catalyzed cycloaddition reaction between azides and 1-iodoalkynes to yield 5-iodo-1,4,5-trisubstituted-1,2,3-triazoles in one step. This is a significant advantage as the reaction yields a product that is directly amenable to further functionalizations. However, there are many lingering questions of its mechanism, which is thought to be distinct from that of the proteo-analog. Competition studies reacting 1-iodoalkynes and terminal alkynes revealed a distinct monopoly effect with exclusive iodotriazole formation followed by proteotriazole generation. In-depth mechanistic studies have been taken facilitated with a custom-built automated reaction sampling prototype to determine the underlying cause of this monopoly. The results of this study as well as engineering considerations of the technology will be discussed in this poster presentation.

Investigating catalyst monopoly in the copper(I)-catalyzed azide-iodoalkyne cycloaddition with automated in situ reaction monitoring technology

253rd National Meeting (2017)

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