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

随着药物、杀虫剂、聚合物和食品添加剂的发现，有机合成成为一门强大的科学，在过去的一个世纪里，它帮助我们现代社会的预期寿命和生活水平大幅提高。硼酸是一种稳定无毒的合成化合物，在过去的二十年里才有了巨大的发展。硼酸的合成和生物应用只有在对其性质和反应性进行明智的探索的支持下才会持续增长。有鉴于此，将在下列方向进行新的项目：合成方法发展：我们对立体化学（选择性制备手性（不对称）化合物的“镜像”形式，这在制药工业中至关重要）的兴趣将集中在饱和单、二、三硼基化合物的具有挑战性的交叉偶联。催化交叉偶联是获得诺贝尔奖（2010）的一类化学反应，作为一种在制药工业中产生新型有机分子的方式，它产生了巨大的影响。饱和分子的立体选择性交叉偶联有助于简化手性药物的合成。2. 新的催化过程：我们将研究硼酸作为温和的和“绿色”催化剂的芳香烷基化通过醇活化的新应用。3. 新型生物正交偶联化学：硼酸盐与刚性二醇的形成提供了一种罕见的生物正交水中自发脱水缩合的情况，并且不需要有毒催化剂。我们将优化一个“点击”偶联系统，它可能成为化学生物学和表面科学的一个选择系统。4. 天然材料的功能化：在加拿大发现的可再生自然资源的价值最大化有着巨大的兴趣。纳米晶纤维素（NCC）是纸浆和造纸工业的木质生物质副产品。这种有趣的材料面临的一个挑战是其表面功能化，特别是使其更具疏水性以扩大其应用范围。我们在硼酸化学方面的知识将被用于设计NCC可控和可逆功能化的试剂。

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.