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Abstract:

Nature uses oxidative couplings to construct carbon-carbon, carbon-oxygen, and carbon-nitrogen bonds with a high degree of efficiency. Few laboratory equivalents are as selective or as efficient as the biological versions. The use of parallel microscale screening to discover selective and efficient catalysts for such processes using oxygen as the terminal oxidant will be discussed.  The outcomes obtained highlight the value of interrogating large numbers of rationally selected variables under the umbrella of general hypothesis. The development of selective catalytic processes for, phenol coupling, asymmetric phenol coupling, alkenyl phenol coupling, and alkyl C–H activation that utilize oxygen as the terminal oxidant will be discussed. These studies have also led to the development of complimentary process that allows the efficient generation of hydrogen peroxide from oxygen. Applications to the total syntheses of honokiol, chaetoglobin, and pyrolaside B will be presented. Finally, studies on the mechanisms of these transformations will be described with the goal of understanding the governing principles and how they might be used to discover further new transformations.