N-Methyliminodiacetic acid Tethered Directing Groups for the Diverse Meta and Para C(sp2)-H Functionalisation of Aryl Boronic Acids and Beyond

用于芳基硼酸等多种间位和对位 C(sp2)-H 官能化的 N-甲基亚氨基二乙酸束缚导向基团

• 批准号: 2457658
• 金额: --
• 依托单位: Imperial College London
• 依托单位国家: 英国
• 项目类别: Studentship
• 财政年份: 2020
• 资助国家: 英国
• 起止时间: 2020 至 无数据
• 项目状态: 未结题
• 来源: https://gtr.ukri.org/projects?ref=studentship-2457658
• 关键词: Methyliminodiacetic; acid; Tethered; Directing; Groups

Boronic acids are ubiquitous building blocks in organic synthesis, due to their ease of handling and broad synthetic versatility. Complex boronic acids can be difficult to access however, due to the reactive promiscuity of the boronic acid functionality. Previous work within the group has led to the design of a dual protecting-directing group for aryl boronic acids. Based on the N-methyliminodiacetic acid (MIDA) protecting group, it stabilizes the parent aryl boronic acid, while directing meta C-H alkenylations, acetoxylations and arylations. This has allowed access to numerous novel boronic acid building blocks for use in total synthesis or medicinal chemistry, and to iterative processes to access valuable polysubstituted aromatics. This project aims to build on this work by expanding the toolbox of C-H functionalisations possible with the directing group, by developing a cognate dual protecting-directing group to selectively direct to the para position., and extending the concept to alkenyl, alkynyl and alkyl substrates.

硼酸是有机合成中普遍存在的结构单元，由于它们易于处理和广泛的合成通用性。然而，由于硼酸官能团的反应性混杂，复合硼酸可能难以获得。该小组以前的工作已经导致了芳基硼酸的双重保护-导向基团的设计。基于N-甲基亚氨基二乙酸（MIDA）保护基，其稳定母体芳基硼酸，同时指导Meta C-H烯基化、乙酰氧基化和芳基化。这使得可以获得许多用于全合成或药物化学的新型硼酸结构单元，以及获得有价值的多取代芳族化合物的迭代方法。该项目旨在通过开发同源的双重保护-指导基团以选择性地指导对位来扩展可能的C-H官能化的工具箱，从而建立这项工作。并将该概念扩展到烯基、炔基和烷基底物。