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

硼酸是有机合成中普遍存在的组成部分，因为它们易于处理和广泛的合成多功能性。然而，由于硼酸官能团的反应性混杂，复杂的硼酸可能很难获得。该小组以前的工作导致了芳基硼酸的双重保护-导向基团的设计。它以N-甲基亚胺二乙酸(MIDA)保护基团为基础，稳定母体芳基硼酸，同时指导间位C-H烷基化、乙酰氧基化和芳基化反应。这使得可以获得许多用于全合成或药物化学的新型硼酸构建块，以及用于获得有价值的多取代芳烃的迭代过程。该项目旨在通过扩展C-H官能化工具箱和导向基团，开发具有选择性地定向到对位的同源双保护-导向基团，并将这一概念扩展到烯基、炔基和烷基底物，从而在此工作的基础上再接再厉。

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.