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

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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.