SusChEM - Sustainable Organic Synthesis Through Aerobic Carbon-Hydrogen Bond Functionalization Reactions

SusChEM - 通过有氧碳氢键功能化反应进行可持续有机合成

• 批准号: 1362396
• 负责人: Paul Floreancig
• 金额: $ 45万
• 依托单位: University of Pittsburgh
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-09-01 至 2019-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1362396&HistoricalAwards=false
• 关键词: SusChEM; Sustainable; Organic; Synthesis; Through

In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Paul Floreancig of the University of Pittsburgh is developing environmentally benign approaches to oxidative bond forming reactions in organic synthesis. The advance is achieved through the use of inexpensive, non-toxic stoichiometric oxidants to regenerate quinones and through new transformations that significantly shorten the synthesis of biologically active molecules and their analogs. These efforts provide new routes to access complex structures through carbon-hydrogen bond functionalization in a manner that minimizes waste generation. Professor Floreancig is traveling to colleges and universities that have high populations of students from groups that are traditionally underrepresented in the STEM fields to give seminars and to engage these students in discussions about scientific careers. In addition, Dr. Florencig will use the results of the research carried out under this award as the basis for lectures on green oxidation chemistry. This project focuses on merging the exceptional capacity to access stabilized carbocations through carbon-hydrogen bond cleavage by the oxidant 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with the environmental benefits of visible light-mediated photooxidation. DDQ is commonly used in stoichiometric quantities and generates significant quantities of reduction product waste. Visible light-mediated oxidations employ environmentally benign stoichiometric oxidants but do not show broad scope in oxidative cation formation. Using visible light-mediated oxidations to regenerate DDQ from the reduction product provides a path to retaining reactivity while reducing waste formation. Investigating several catalyst systems allow determination of the ideal catalyst structures for this new strategy.

在化学部化学综合计划资助的该项目中，匹兹堡大学的Paul Floreancig教授正在开发环境良性的方法，以形成有机合成中的氧化键反应。通过使用廉价的，无毒的化学计量氧化剂来再生奎因酮，以及通过显着缩短生物活性分子及其类似物的合成的新变化来实现进步。这些努力为通过碳氢键功能化提供了新的途径，以最大程度地减少废物产生的方式来访问复杂的结构。 Floreancig教授正在前往学院和大学，这些大学的学生人数众多，这些学生来自STEM领域中传统上人数不足的团体，以举办研讨会，并让这些学生参与有关科学职业的讨论。此外，Florencig博士将使用根据该奖项进行的研究结果作为绿色氧化化学讲座的基础。该项目的重点是通过氧化剂2,3-二氯-5,6-二氯1,4-苯二醌（DDQ）与可见的光介导光介导的光学介导的氧化剂搭配，通过氧化剂2,3-二氯-5,6-二氯-1,4-苯甲酮（DDQ）通过碳氧化键裂解来融合稳定的碳化力。 DDQ通常用于化学计量量，并产生大量的还原产品废物。可见的光介导的氧化作用采用环境良性化学计量氧化剂，但在氧化阳离子形成中没有显示较大的范围。使用可见的光介导的氧化从还原产物中再生DDQ，这为保持反应性提供了一条途径，同时减少废物的形成。研究多个催化剂系统允许确定这种新策略的理想催化剂结构。