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Electrochemistry as an enabling tool for reaction discovery

电化学作为反应发现的有利工具

基本信息

批准号：
10659868
负责人：
Song Lin
金额：
$ 34.96万
依托单位：
CORNELL UNIVERSITY
依托单位国家：
美国
项目类别：
财政年份：
2018
资助国家：
美国
起止时间：
2018-09-20 至 2027-08-31
项目状态：
未结题

项目摘要

Project Summary This proposal focuses on using electrochemistry as an unconventional tool to uncover new organic reactions and invent synthetic strategies with the goal of facilitating the preparation of bioactive compounds. Improving the organic synthesis of medicinally active compounds is crucial to modern biomedical research. In this context, oxidation and reduction reactions are among the most important and frequently used processes in organic synthesis. However, manipulating the oxidation states of functional groups in complex settings with high efficiency, precision, and minimal waste remains an important challenge in modern organic chemistry. Given its many distinct characteristics, electrochemistry represents an attractive approach to discovering new reactivities, enabling new synthetic strategies, and meeting the prevailing trends in organic synthesis. Therefore, there exists a clear impetus for the invention of new reaction strategies to improve the scope of synthetic electrochemistry and provide new platforms for reaction discovery and synthetic innovations. In the past funding period, we demonstrated a new catalytic approach that combines electrochemistry and redox-metal catalysis for the oxidative difunctionalization of alkenes to access a diverse array of highly functionalized structures. These promising results led us to envision that electrochemistry will ultimately emerge as a powerful tool for solving a wide range of longstanding synthetic problems. In the new funding cycle, we aim to build upon our previous success but move our research into new grounds. In each of the projects targeted herein, we aim to apply electrochemistry to address a prominent challenge in organic synthesis. The transformations targeted in this grant are either currently unknown or display salient limitations in reaction scope or selectivity. Among the specific reactions that we aim to develop in the context of this grant are: two- and three-component cross-electrophile couplings; asymmetric synthesis and late-stage functionalization of N-containing compounds; and regioselective C–H functionalization of pyridines. In addition, in-depth studies using canonical physical organic and electroanalytical techniques will provide insights into the reaction mechanisms. The development and mechanistic understanding of these proposed transformations will represent significant advances for the field of organic synthesis.

项目摘要这项提案的重点是利用电化学作为一种非传统的工具，以发现新的有机反应和发明合成策略，目的是促进生物活性物质的制备。化合物.改进药用活性化合物的有机合成对现代生物技术至关重要。生物医学研究在这种情况下，氧化和还原反应是最重要的反应之一，有机合成中常用的方法。然而，操纵功能的氧化态，高效率、高精度和最小浪费的复杂环境中的群体仍然是重要的现代有机化学的挑战鉴于其许多独特的特点，电化学代表了一种有吸引力的方法来发现新的反应性，实现新的合成策略，符合有机合成的主流趋势。因此，有一个明确的动力，发明新的反应策略，以改善合成电化学的范围，并提供新的反应发现和合成创新的平台。在过去的一段时间里，我们展示了一种新的催化方法，结合电化学和氧化还原金属催化的氧化烯烃的双官能化以获得多种高度官能化的结构。这些有希望的结果使我们设想，电化学最终将成为一种强大的工具，解决了一系列长期存在的合成问题。在新的融资周期中，我们的目标是我们以前的成功，但我们的研究进入新的领域。在本文所针对的每一个项目中，我们的目标是应用电化学来解决有机合成中的一个突出挑战。的本补助金所针对的转型要么是目前未知的，要么是在反应中显示出明显的局限性。范围或选择性。我们旨在在此赠款背景下制定的具体反应包括：二组分和三组分交叉亲电偶联;不对称合成和后期含N化合物的官能化;和吡啶的区域选择性C-H官能化。在此外，使用典型的物理有机和电分析技术进行深入研究，将提供对反应机制的理解。这些的发展和机械理解所提出的转化将代表有机合成领域的重大进展。