Oxidative aromatization is an appealing method for the preparation of aromatic heterocycles, (including substituted pyridines, benzothiazoles, benzimidazoles, and benzoxazoles) from cheap and common molecular building blocks. While hundreds of methods exist, most include the use of elevated temperatures, transition metal catalysts, or strong and costly oxidants. With inspiration from natural flavoprotein oxidases, which convert prearomatic nicotinamide to a stable pyridinium and are fueled by O2 as the terminal oxidant, a wide range of heteroaromatic species with broad substitution patterns was acheived. Aromatic stabilization, hydride donor capability, heteroatom oxidation, and fine-tuned flavin-derived catalysts provide a general and efficient method that is metal-free and functions at ambient temperatures for the preparation of a broad range of heteroaromatic core structures.  This talk will describe the catalytic details, scope, practical limitations, and lessons from natural oxidative aromatizations.

Biomimetic preparation of aromatic heterocycles: Mild, aerobic, single-pot syntheses based on nicotinamide-flavin-O<sub>2</sub> catalytic redox systems

248th National Meeting (2014)

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Biomimetic preparation of aromatic heterocycles: Mild, aerobic, single-pot syntheses based on nicotinamide-flavin-O2 catalytic redox systems

Biomimetic preparation of aromatic heterocycles: Mild, aerobic, single-pot syntheses based on nicotinamide-flavin-O₂ catalytic redox systems