CAREER: Expanding the Toolbox for Olefin Functionalization and Difunctionalization Reactions

在化学系化学合成项目的支持下，托莱多大学的Michael Young正在开发新的方法，通过使用反应添加剂来控制区域化学，在烯烃的两个碳原子上安装新的分子片段。烯烃是从石化和生物基来源获得的常见原料化学品。尽管已经研究了许多现有的策略来将烯烃结构单元选择性地转化为增值产物，但仍然存在与产物混合物的形成相关的挑战和对浪费的中间合成步骤的需要。Young博士和他的研究团队正致力于用简单而丰富的反应添加剂（如二氧化碳）控制烯烃的反应。这些研究有可能允许更有效地合成用于新药、精细化学品和下一代材料的有价值的化学结构单元。Young博士还将向研究生和教学实验室介绍溶剂回收的实践，以强调可持续发展的重要性。此外，还为学生和当地化工行业员工开发了关于绿色化学原理的在线短期课程。导向基团在推进C-H官能化领域中发挥了重要作用，瞬态导向基团的开发继续提高这一实现选择性反应性的重要策略的合成效率。Michael Young博士和他的学生正在开发使用瞬态定向基团工具进行内烯烃官能化策略的方法。具体地说，区域选择性芳基化的游离胺系烯烃与芳基卤化物正在研究通过改变反应条件。该方法旨在提高内烯烃芳基化反应的选择性并促进产物多样化。此外，还将研究活化烯烃的1，2-双官能化反应，以在同一步骤中安装C-C和C-O/C-N键。机制研究计划指导优化和合成应用这种新的化学。预计这些活动将为含胺化合物的快速多样化提供新的方法，这有利于开发化合物库，以支持制药和农用化学品工业。这些活动还将为研究生、本科生和高中生以及博士后研究人员提供合成和有机金属化学方面的优秀培训基地。该奖项反映了NSF的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis Program in the Division of Chemistry, Michael Young of The University of Toledo is developing new ways to install new molecular fragments at both carbon atoms of an alkene by using reaction additives to control the regiochemistry. Alkenes are common feedstock chemicals that are obtained from both petrochemical and bio-based sources. Despite the many existing strategies that have been studied for selectively converting alkene building blocks into value-added products, there are still challenges associated with the formation of product mixtures and the need for wasteful intermediate synthetical steps. Dr. Young and his research team are working to control the reactions of alkenes with simple and abundant reaction additives such as carbon dioxide. These studies have the potential to permit for more efficient syntheses of valuable chemical building blocks for new pharmaceuticals, fine chemicals, and next generation materials. Dr. Young will also introduce the practice of solvent recycling to research students and into teaching labs to emphasize the importance of sustainability. In addition, online short courses on green chemistry principles are also being developed for students and the local chemical industry workforce.Directing groups have played an essential role in advancing the field of C-H functionalization and the development of transient directing groups continues to improve the synthetic efficiency of this important strategy for achieving selective reactivity. Dr. Michael Young and his students are developing ways to use transient directing group tools for internal olefin functionalization strategies. Specifically, the regioselective arylation of free amine-tethered alkenes with aryl halides is being investigated by changing reactions conditions. This approach is designed to both improve the selectivity of internal alkene arylation reactions and facilitate product diversification. In addition, 1,2-difunctionalization reactions of activated alkenes will be studied to install C-C and C-O/C-N bonds in the same step. Mechanistic studies are planned to guide optimization and synthetic application of this new chemistry. These activities are expected to provide new approaches to the rapid diversification of amine-containing compounds, which is beneficial for developing compound libraries to support the pharmaceutical and agrochemical industries. These activities will also provide an excellent training ground in synthetic and organometallic chemistry for a diverse group of graduate, undergraduate, and high school students, as well as a postdoctoral researcher.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.