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

硼酸是无处不在的积木在有机合成，由于他们易于处理和广泛的合成通用性。然而，由于硼酸功能的反应性混乱，复杂的硼酸很难获得。该小组之前的工作导致了芳基硼酸双保护导向组的设计。它以n -甲基二乙酸（MIDA）保护基团为基础，稳定母体芳基硼酸，同时引导间位C-H烯基化、乙酰氧基化和芳基化。这使得在全合成或药物化学中使用的许多新型硼酸构建块，以及获得有价值的多取代芳烃的迭代过程成为可能。本项目旨在通过扩展C-H功能化工具箱，通过开发一个同源的双重保护-定向组来选择性地指向para位置，从而建立在这项工作的基础上。，并将概念扩展到烯基、炔基和烷基底物。

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.