Acceptor-Acceptor Carbenoids in Selective Insertions and Cyclizations

选择性插入和环化中的受体-受体类胡萝卜素

• 批准号: 1465113
• 负责人: Jon Rainier
• 金额: $ 45万
• 依托单位: University of Utah
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-07-15 至 2019-05-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1465113&HistoricalAwards=false
• 关键词: Acceptor; Carbenoids; Selective; Insertions; Cyclizations

With this award, the Chemical Synthesis Program is supporting Professor Jon Rainier at the University of Utah to study the conversion of vinyl diazophosphonates and diazo vinylphosphonates into acceptor-acceptor Rh carbenes and use the carbenes in insertion reactions with alcohols, amines, and thiols. Included in this work will be the examination of novel substrates and reactions having unique properties. The inspiration for many of these substances and reactions came from both naturally and non-naturally occurring small molecules that have been shown to be biologically active. As a consequence, these studies will generate new materials of potentially high impact in the chemical and pharmaceutical industry. Professor Rainier will integrate the research and educational components of this project into the teaching curriculum at the University of Utah as well as into his work with the American Chemical Society Student Affiliates. By bringing research projects into the undergraduate curriculum, Professor Rainier hopes to inspire the next generation of scientists to careers in chemistry. Through his involvement with the Student Affiliates, Professor Rainier has reached out to many elementary and middle school students through hands on experiments, workshops and demonstrations in an attempt to promote curiosity and STEM education. In this research, new methods involving acceptor-acceptor vinyl carbenes will be developed for the synthesis of phosphonate containing materials and small molecules. The work that will be carried out in pursuit of these goals is unique in that it will both provide a better fundamental understanding of the properties of phosphonate containing carbenes and in that it will have practical value. Professor Rainier and his group will explore the effect of electronic and steric perturbations on metal carbenes and substrates on the insertion chemistry of vinyl diazophosphonates. Over the course of this work, a range of phosphonate-containing small molecules will be generated. Preliminary evidence suggests that these products may have potential as bioactive small molecules and as ligands for functionalized iron nanoparticles, themselves with possible application in the delivery of small molecules and genes in biological systems.

有了这个奖项，化学合成计划正在支持教授乔恩雷尼尔在犹他州的大学研究乙烯基重氮膦酸酯和重氮乙烯基膦酸酯转化为受体受体铑卡宾和使用卡宾插入反应与醇，胺和硫醇。 包括在这项工作将是新的基板和具有独特性能的反应的检查。许多这些物质和反应的灵感来自天然和非天然存在的小分子，这些小分子已被证明具有生物活性。因此，这些研究将产生在化学和制药行业具有潜在高影响力的新材料。Rainier教授将把该项目的研究和教育部分整合到犹他州大学的教学课程中，并与美国化学学会学生分会合作。通过将研究项目纳入本科课程，雷尼尔教授希望激励下一代科学家从事化学职业。通过与学生联盟的合作，Rainier教授通过动手实验、研讨会和演示接触了许多中小学生，试图促进好奇心和STEM教育。在本研究中，将开发新的方法，包括受体-受体乙烯基卡宾合成含膦酸酯的材料和小分子。为实现这些目标而开展的工作是独特的，因为它将提供对含卡宾膦酸酯性质的更好的基本理解，并且具有实用价值。Rainier教授和他的团队将探索电子和空间位阻扰动对金属卡宾和底物的影响，以及乙烯基重氮膦酸酯的插入化学。在这项工作的过程中，将产生一系列含膦酸酯的小分子。初步证据表明，这些产品可能具有潜在的生物活性的小分子和功能化的铁纳米粒子的配体，在生物系统中的小分子和基因的传递本身与可能的应用。