This work utilizes non-precious metal catalysts to form new bonds in the context of heterocycle synthesis. Complex heterocycles can impart desirable properties in molecules used across chemical disciplines and industries. As such, practical methods to synthesize heterocycles in high yields, under mild conditions, and with a variety of functional groups are of great interest to academic and industrial researchers alike. Research in this group has discovered that copper (I) iodide catalyzes the hydroamination of propargyl imidates, propargyl thioimidates, and other imino-alkyne substrates at room temperature. The reaction products are the non-aromatic dihydro-azoles, rather than the fully aromatized heterocycles. These open-flask reactions use low catalyst loadings (1 to 5 mol%), proceed with complete conversion, and require minimal purification (filtration). The isolated non-aromatic compounds react with a variety of electrophiles with concomitant aromatization forming highly functionalized heterocycles not easily accessible via current methods. Structure/activity relationship data will be presented to support a proposed general mechanism for these reactions.

Heterocycle formation via imino-alkyne hydroamination

ACS Fall 2021

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