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

在这个由化学部化学合成项目资助的项目中，匹兹堡大学的Paul Floreancig教授正在开发有机合成中氧化键形成反应的环保方法。这一进展是通过使用廉价、无毒的化学计量氧化剂来再生醌，并通过新的转化，大大缩短了生物活性分子及其类似物的合成。这些努力为通过碳氢键功能化获得复杂结构提供了新的途径，从而最大限度地减少了废物的产生。弗洛朗西格教授正在前往那些拥有大量学生的学院和大学，这些学生来自传统上在STEM领域代表性不足的群体，并举办研讨会，让这些学生参与有关科学职业的讨论。此外，Florencig博士将使用在该奖项下进行的研究结果作为绿色氧化化学讲座的基础。该项目的重点是将氧化剂2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）通过碳氢键裂解获得稳定碳阳离子的特殊能力与可见光介导的光氧化的环境效益结合起来。DDQ通常用于化学计量量，并产生大量的还原产物废物。可见光介导的氧化使用环境无害的化学计量氧化剂，但在氧化阳离子形成中没有显示出广泛的范围。利用可见光介导的氧化从还原产物中再生DDQ提供了一条在减少废物形成的同时保持反应性的途径。研究几种催化剂体系可以确定这种新策略的理想催化剂结构。

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.