Molecular hydrogen is the ideal stoichiometric reductant due to its excellent atom- and mass-economy. Typically, transition metals are the primary reactants utilized to facilitate these transfer hydrogenations due to their ability to activate and transfer H<sub>2</sub> to important synthetic precursors. Conversely, nature employs organic cofactors, NADH and NADPH, as reductants in performing hydride-mediated reactions. Pyridinium-derived carbenes have been developed, which upon insertion into molecular hydrogen form dihydropyridines, to serve as a biomimetic in the process of these important reductive transformations. Experiments designed to study the importance of carbene structure, solvent, temperature, hydrogen pressure, as well as the structure of the carbene precursor in hydrogenations will be presented. The operating mechanism will be described in detail.

Mechanistic complexities of catalytic dihydropyridine reactions

253rd National Meeting (2017)

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