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CAREER: New Dearomative Methods and Strategies for Organic Synthesis

职业：有机合成的新脱芳香方法和策略

基本信息

批准号：
1654110
负责人：
David Sarlah
金额：
$ 62.4万
依托单位：
University of Illinois at Urbana-Champaign
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2017
资助国家：
美国
起止时间：
2017-02-01 至 2022-01-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1654110&HistoricalAwards=false
关键词：
CAREER New Dearomative Methods Strategies

项目摘要

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.

在美国国家科学基金会化学合成计划的支持下，David Sarlah教授正在开发一种新颖实用的反应，用于选择性地用六元环中的单键取代碳-碳双键，这一过程被称为脱芳功能化。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之间的差距，这是一个广泛研究的领域，芳香族化合物的化学，在一个六元环中有三个这样的双键。用单键代替双键可以使廉价、容易获得的化合物快速、可控地转化为高价值、复杂的分子。这项工作在有机合成和药物化学等领域具有广泛的应用前景。这个项目在概念上很有趣，有许多潜在的应用，使它非常适合各级科学家的教育。萨拉教授还开创了一项外展计划，即行动中的科学（SIA），为伊利诺伊州大香槟地区代表性不足的学生提供关键的动手科学教育。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有益的科学体验。脱芳化反应是有机合成中一类重要的转化反应。这些转化将现成的芳烃转化为具有多种用途的有用合成中间体。尽管大多数现代脱芳工艺没有将功能纳入芳香框架，但该研究旨在开发一种通用的脱芳方法，从而能够引入广泛的官能团。具体来说，本研究描述了小分子的脱芳光环加成，使所得到的环加合物的原位烯烃型化学反应成为各种部分不饱和的功能化产物。通过随后的操作，该策略允许获得各种取代环己烯和二、三或四取代环己烯，否则难以通过已知方法获得。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“科学在行动”计划的发展，该计划为伊利诺伊州中部的低收入学校带来了可接受的科学教育。在当地教师和其他UIUC研究小组的帮助下，最初的示范项目已经扩展到更广泛的受众，并扩展到更广泛的科学主题。