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

“硼酸的新合成方法及其在立体选择性交叉偶联、催化和化学生物学中的应用”

• 批准号: 203287-2012
• 负责人: Hall, Dennis
• 金额: $ 10.2万
• 依托单位: University of Alberta
• 依托单位国家: 加拿大
• 项目类别: Discovery Grants Program - Individual
• 财政年份: 2015
• 资助国家: 加拿大
• 起止时间: 2015-01-01 至 2016-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=569921
• 关键词: New; Synthetic; Methods; Applications; Boronic

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.

随着药物、杀虫剂、聚合物和食品添加剂等发现的出现，有机合成成为一门强大的科学，在过去的一个世纪里帮助我们的现代社会享受到了预期寿命和生活水平的显著提高。硼酸是一种稳定无毒的合成化合物，在过去20年里才经历了巨大的发展。只有在对硼酸的性质和反应性进行明智的探索的情况下，硼酸的合成和生物应用才会持续增长。根据这一观点，将在以下方向开展新的项目：1.合成方法学的发展：我们对立体化学(选择性制备在制药工业中至关重要的“镜像”形式的手性(不对称)化合物)的兴趣将集中在饱和的一、二和三硼化合物的具有挑战性的交叉偶联上。催化交叉偶联是2010年获得诺贝尔奖的一类化学反应，在制药业中作为一种产生新型有机分子的方法产生了巨大的影响。饱和分子的立体选择性交叉偶联有助于手性药物的合成。2.新的催化方法：我们将研究硼酸作为温和的绿色催化剂在芳香族醇烷基化反应中的新应用。3.新颖的生物正交结合化学：与刚性二醇形成硼酸盐提供了一种罕见的在生物正交的水中自发脱水缩合的情况，而且它不需要有毒的催化剂。我们将优化‘点击’连接系统，这可能成为化学生物学和表面科学的一种选择系统。4.自然材料的功能化：加拿大对最大限度地利用可再生自然资源的价值有着巨大的兴趣。纳米纤维素(NCC)是制浆造纸工业的木质生物质副产品。这种耐人寻味的材料的一个挑战是它的表面功能化，特别是使它更疏水以扩大其应用。我们将利用我们在硼酸化学方面的知识，为NCC的可控和可逆官能化设计试剂。