CAREER: New Dearomative Methods and Strategies for Organic Synthesis

在国家科学基金会化学合成计划的支持下，David Sarlah教授正在开发新的、实用的反应，用于选择性地将碳-碳双键替换为六元环中的单键，这一过程被称为脱芳官能化。萨拉教授是伊利诺伊大学香槟分校(UIUC)化学系的教员。这项工作的基本主题是弥合碳-碳双键化学和芳香化合物化学之间的差距，碳-碳双键化学是一个被广泛研究的领域，芳香化合物化学在一个六元环中有三个这样的双键。用单键取代双键，可以快速、可控地将廉价、容易获得的化合物转化为高价值的复杂分子。这项工作在有机合成和药物化学方面具有广阔的应用前景。该项目在概念上很有趣，并有许多潜在的应用，使其非常适合各级科学家的教育。萨拉教授还开创了一个名为科学在行动(SIA)的推广计划，为伊利诺伊州大香槟地区未被充分代表的学生提供重要的实践科学教育。通过SIA项目，该系的研究生与当地教师合作，为低收入学校的孩子们带来富有启发性的科学经验。脱体反应是有机合成中的一类重要转化。这些转化将容易获得的芳烃转化为具有不同应用的有用的合成中间体。虽然大多数现代脱芳烃工艺没有将官能团引入芳烃骨架，但拟议的研究旨在开发一种通用的脱芳方法，使其能够引入广泛的官能团。具体地说，这项研究描述了小分子的脱芳族光环加成反应，使所产生的环加成物能够以原位烯烃类型的化学方式生成各种部分不饱和的官能化产品。通过随后的操作，该策略允许获得各种取代的环己二烯和二、三或四取代的环己烯，否则很难通过已知的方法获得它们。这类产品是制备药品、农用化学品和其他精细化学品的有用中间体。该项目的教育部分包括制定科学行动计划，该计划为伊利诺伊州中部的低收入学校提供可获得的科学教育。在当地教师和UIUC其他研究小组的帮助下，最初的模型项目已扩展到更广泛的受众，并扩展到更广泛的科学主题。

With the support of the Chemical Synthesis Program of the National Science Foundation, Professor David Sarlah is developing novel, practical reactions for the selective replacement of carbon-carbon double bonds with single bonds in six-membered rings, a process described as dearomative functionalization. Professor Sarlah is a faculty member in the Department of Chemistry at the University of Illinois, Urbana-Champaign (UIUC). The underlying theme of the work is to bridge the gap between the chemistry of carbon-carbon double bonds, an extensively studied area, and the chemistry of aromatic compounds, which have three such double bonds in a six-membered ring. Replacing the double bonds with single bonds allows for the rapid and controlled conversion of cheap, readily accessible compounds into high-value, complex molecules. This work may have broad applications in organic synthesis and medicinal chemistry. The project is conceptually interesting and has many potential applications, making it well suited for the education of scientists at all levels. Professor Sarlah is also pioneering an outreach program, Science in Action (SIA), that provides crucial hands-on science education for underrepresented students in the greater Champaign, IL area. Through the SIA program, graduate students in the department, in collaboration with local teachers, bring instructive science experiences to children in low-income schools.Dearomatization reactions are an important class of transformations in organic synthesis. These transformations convert readily available arenes into useful synthetic intermediates with diverse applications. Whereas most modern dearomatization processes do not incorporate functionality into the aromatic framework, the proposed research aims to develop a general dearomative method that enables introduction of a wide range of functional groups. Specifically, this research describes the dearomative photocycloaddition of small molecules that enables in situ alkene-type chemistry of the resulting cycloadducts into a diverse array of partially unsaturated, functionalized products. With subsequent manipulations, this strategy permits access to a variety of substituted cyclohexadienes and di-, tri-, or tetrasubstituted cyclohexenes that are otherwise difficult to access through known methods. These classes of products are useful intermediates in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. The educational component of this project includes the development of the Science in Action program, which brings accessible science education to low-income schools in central Illinois. With the help of local teachers and other UIUC research groups, the initial model program has been expanded to reach a broader audience and extended to a wider range of science topics.