Molecular oxygen is one of the most attractive oxidants available for chemical synthesis, but few aerobic oxidation methods exhibit sufficient scope and utility to be considered for large-scale production of pharmaceuticals and fine chemicals. In addition, the combination of organic chemicals with O2 presents significant safety concerns, and this issue is a significant barrier to the use of O2 in process-scale synthesis. Recent research in our laboratory targets solutions to these challenges. Fundamental studies of catalytic reactions have provided a foundation for development of diverse aerobic oxidation reactions. In particular, highly practical methods have been identified for the oxidation of alcohols to aldehydes, ketones, carboxylic acids, esters, and nitriles. These reactions exhibit sufficient catalytic efficiency and functional group compatibility to offer compelling aerobic alternatives to traditional oxidation methods. A 2007-2009 collaboration with Eli Lilly led to the development of a continuous flow process for safe and scalable aerobic oxidation reactions. Shortly thereafter, we joined forces with Prof. Thatcher Root (UW-Madison, Chemical and Biological Engineering), Eli Lilly, Merck and Pfizer to identify solutions to additional challenges facing process-scale implementation of aerobic oxidation. This talk will focus on recent developments of catalytic aerobic oxidation methods and practical issues associated with large-scale applications of this chemistry.

Catalytic aerobic oxidation of organic chemicals: From fundamental studies to industrial relevance

247th National Meeting (2014)

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