Catalytic Difunctionalization of Alkenes and Dienes

烯烃和二烯的催化双官能化

• 批准号: 1266359
• 负责人: Forrest Michael
• 金额: $ 37.5万
• 依托单位: University of Washington
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2013
• 资助国家: 美国
• 起止时间: 2013-07-15 至 2017-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1266359&HistoricalAwards=false
• 关键词: Catalytic; Difunctionalization; Alkenes; Dienes

The Chemical Catalysis Program of the NSF Division of Chemistry supports the efforts of Professor Forrest Michael of the Department of Chemistry at the University of Washington to design and study palladium-based catalysts for the direct addition of nitrogen-containing functional groups to alkenes and dienes under oxidative conditions. Specific focus is directed towards reactions that generate new C-N bonds; minimize the formation of by-products; that are tolerant of air, water, and complex functional groups; that operate under mild conditions; and that are highly stereoselective. For example, reactions that result in the amination of dienes are explored, as well as a new classes of reaction predicated on the reaction of intermediate palladium allyl complexes with electrophiles. Additionally, the difunctionalization of alkenes is achieved via the catalytic ring-opening reactions of aziridines. The importance of mechanistic understanding in reaction development is an emphasis area. The synthetic tools developed in studying these alkene and diene additions allows for the synthesis of a wide variety of densely functionalized products from simple starting materials. The development of new, efficient metal-catalyzed oxidative amination reactions has significant applications in diverse fields including the development of new materials, the synthesis of pharmaceuticals and other bioactive compounds, and the construction of new tools and probes for investigating important problems in biology and medicine. The potential control of regio- and stereochemistry informs the formation of complex and biologically-relevant compounds. Professor Michael implements Process Oriented Guided Inquiry Learning (POGIL) techniques to encourage content retention and analytical thinking in courses that he teaches. He also works with programs for gifted high school students such as the Research Science Institute and the Saudi Research Science Institute, administered by the Center for Excellence in Education, the Accelerated Progress Program at Garfield High School in Seattle, and the Gifted High School Program in Bellevue. In this role, he presents short lectures and demonstrations on the importance of and exciting new developments in modern chemistry and recruits these students into laboratory research. Professor Forrest Michael of the Department of Chemistry at the University of Washington and his research group are engaged in chemical research to help develop and understand ways of building complex, biologically-relevant molecules. The research group investigates ways to incorporate nitrogen-containing functional groups to molecules that contain double and triple carbon-carbon bonds. Such products are important in the field of small molecule based medicine and chemical biology and thus, new methods for achieving such targeted molecules that are more efficient and reliable are highly desirable. This research project provides education and training opportunities for students at the high school, college, and graduate level, helping create a pipeline of new scientists.

NSF化学部的化学催化计划支持华盛顿大学化学系的Forrest Michael教授设计和研究钯基催化剂，用于在氧化条件下将含氮官能团直接加成到烯烃和二烯上。 特别关注的是产生新的C-N键的反应;最大限度地减少副产物的形成;耐受空气，水和复杂的官能团;在温和的条件下操作;并且具有高度立体选择性。 例如，探索导致二烯胺化的反应，以及基于中间体钯烯丙基配合物与亲电试剂反应的一类新反应。 此外，通过氮丙啶的催化开环反应实现烯烃的双官能化。 在反应发展中理解机理的重要性是一个重点领域。 在研究这些烯烃和二烯加成中开发的合成工具允许从简单的起始材料合成各种各样的密集官能化产物。 新型高效金属催化氧化胺化反应的发展在不同领域具有重要的应用，包括新材料的开发，药物和其他生物活性化合物的合成，以及用于研究生物学和医学中重要问题的新工具和探针的构建。 区域和立体化学的潜在控制通知复杂的和生物相关的化合物的形成。 迈克尔教授实施过程导向的引导探究学习（POGIL）技术，以鼓励他所教授的课程内容保留和分析思维。 他还与天才高中生项目合作，如由卓越教育中心管理的研究科学研究所和沙特研究科学研究所，西雅图加菲猫高中的加速进步项目，以及贝尔维尤的天才高中项目。 在这个角色中，他提出了简短的讲座和演示的重要性和令人兴奋的新发展，在现代化学和招募这些学生进入实验室研究。 华盛顿大学化学系的Forrest Michael教授和他的研究小组从事化学研究，以帮助开发和理解构建复杂的生物相关分子的方法。该研究小组研究了将含氮官能团结合到含有碳碳双键和三键的分子中的方法。 这样的产物在基于小分子的医学和化学生物学领域中是重要的，因此，非常需要更有效和可靠的用于获得这样的靶向分子的新方法。 该研究项目为高中，大学和研究生水平的学生提供教育和培训机会，帮助创建新科学家的管道。