Bismuth(III) acetylides were reported to demonstrate efficient cycloaddition reactivity in the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) forming stable 5-bithmuth(III) triazoles. These bismuth-substituted heterocycles can be further functionalized under mild conditions. We examined electronic and steric effects of different substituents in the diphenyl sulfone ligand as well as at the C2 carbon of the alkyne. The rate and the selectivity of the triazole formation in the presence of copper(I) catalyst were monitored by NMR kinetic measurements and reaction heat flow calorimetry. As in our previous mechanistic study with 1-iodoalkynes, mathematical apparatus of statistical analysis was developed and applied for accurate processing of the kinetic data.<br/>

Mechanistic investigation of reactions of bismuth(III) acetylides with organic azides in the copper(I)-catalyzed cycloaddition reaction

255th National Meeting (2018)

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