"New Synthetic Methods and Applications of Boronic Acids in Stereoselective Cross-Coupling, Catalysis, and Chemical Biology"

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With discoveries like drugs, insecticides, polymers, and food additives, organic synthesis stands as a powerful science that helped our modern society enjoy a dramatic increase in life expectancy and standard of living in the past century. Boronic acids are stable and non-toxic synthetic compounds that have undergone huge developments only over the past two decades. Continued growth in the synthetic and biological applications of boronic acids will occur only if supported by a judicious exploration of their properties and reactivity. With this view, new projects will be undertaken in the following directions: 1. Synthetic methodology development: Our interest in stereochemistry (the selective preparation of "mirror image" forms of chiral (unsymmetrical) compounds, which is of critical importance in the pharmaceutical industry) will focus on the challenging cross-coupling of saturated mono-, di-, and tri-boryl compounds. Catalytic cross-couplings are a Nobel Prize winning (2010) class of chemical reactions that have had a huge impact as a way to generate novel organic molecules in the pharmaceutical industry. Stereoselective cross-couplings of saturated molecules could help streamline the synthesis of chiral drugs. 2. New catalytic processes: We will examine new applications of boronic acids as mild and 'green' catalysts for aromatic alkylations via alcohol activation. 3. Novel bioorthogonal conjugation chemistry: Boronate formation with rigid diols offers a rare case of spontaneous dehydrative condensation in water that is bioorthogonal, and it does not require toxic catalysts. We will optimize a 'click' conjugation system that could become a system of choice in chemical biology and surface sciences. 4. Functionalization of natural materials: There is huge interest in maximizing the value of renewable natural resources found in Canada. Nanocrystalline cellulose (NCC) is a wooden biomass by-product of the pulp and paper industry. One challenge with this intriguing material is its surface functionalization, especially to render it more hydrophobic to expand its applications. Our knowledge of boronic acid chemistry will be exploited to design agents for the controlled and reversible functionalization of NCC.