CAREER: New Dearomative Methods and Strategies for Organic Synthesis

在美国国家科学基金会化学合成计划的支持下，大卫·萨拉教授正在开发新颖的实用反应，用于在六元环中用单键选择性取代碳-碳双键，这一过程被描述为脱芳官能化。 Sarlah教授是伊利诺伊大学厄巴纳-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（一个广泛研究的领域）和芳香族化合物化学（在六元环中有三个这样的双键）之间的差距。用单键取代双键可以使廉价、易得的化合物快速、可控地转化为高价值的复杂分子。这一工作在有机合成和药物化学中有着广泛的应用。该项目在概念上很有趣，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外展计划，科学在行动（SIA），提供了重要的动手科学教育的代表性不足的学生在大尚潘，IL区。通过SIA计划，该部门的研究生与当地教师合作，为低收入学校的孩子们带来了有益的科学经验。去芳化反应是有机合成中重要的一类转化。 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构化过程不将功能性纳入芳族框架，但所提出的研究旨在开发一种通用的脱芳构化方法，该方法能够引入广泛的官能团。具体而言，本研究描述了小分子的脱芳光环加成，其使所得环加合物的原位烯烃型化学反应成为一系列不同的部分不饱和官能化产物。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，否则难以通过已知方法获得。这类产品是制备药物、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，为伊利诺伊州中部的低收入学校提供科学教育。在当地教师和其他UIUC研究小组的帮助下，最初的示范计划已经扩大到更广泛的受众，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.