Caffeine, a well-known alkaloid and central nervous system stimulant, has been used as a nitrogen-donor (and occasionally oxygen-donor) ligand to prepare several transition metal complexes. It has also been used as a precursor to generate N-heterocyclic carbenes (NHCs) and coordination compounds thereof, some of which have found applications in catalytic transformations. This presentation outlines the syntheses, molecular structures, and reactivity of N-heterocyclic thione (NHT) and selone (NHSe) derivatives of caffeine. More specifically, these novel ligands have been used to prepare a number of mercury(II), copper(I), silver(I), and gold(I) complexes, including (CaffEMe)nHgX2 (E = S, Se; n = 1, 2; X = Cl, Br, I) and (CaffEMe)MX (E = S, Se; M = Cu, Au; X = Cl, Br), several of which have been structurally characterized. A combination of 1H NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS) has been used to ascertain the selenophilicity of mercury in this system and the results of these experiments will also be discussed in this presentation.

Synthesis and reactivity of N-heterocyclic chalcogenone derivatives of caffeine

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ACS Fall 2022

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