The aerobic oxidation of organic moleucles is fundamentally important to the chemical industry, but is overwhelmingly limited to the synthesis of relatively simple, large volume chemicals. In more complex settings, the use of O2 is complicated by its triplet electronic structure, 4 electron reduction stoichiometry and small steric profile, which create challenges of chemo- and regioselecitivty. To overcome these challenges, our group has drawn inspriation from the dinuclear copper enzyme tyrosinase, which provides a mechanistic blueprint for the activation of O2 and substrate oxidation with high selectivity. This lecture will describe our group's recent efforts to develop simplified mimics of the tyrosinase active site to serve as robust catalysts for the aerobic oxidation of complex molecules. The talk will underscore mechanistic aspects of these reactions that differ from their enzymatic progenitors, and offer guiding principles for controlling selectivity when using O2 in complex molecule synthesis.

Driving synthesis by oxidation

254th National Meeting (2017)

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