Development of B(MIDA)-based directing groups for C-H functionalization

Lead Research Organisation: Imperial College London
Department Name: Dept of Chemistry

Abstract

The practical advantages of using 'protected' boronic acid derivatives such as B(MIDA) derivatives will be expanded to permit their use as functional directing groups for transition metal catalyzed C-H functionalization ortho of aryl-B(OH)2 derivatives as well as for alkenyl-Csp2 and alkyl-Csp3 functionalizaiton. Givent he wide spread commercialization of these functionalities, we expect that a successful demonstration of these new directing B(MIDA) derivatives will be of importance to chemical industries, including the pharmaceutical, agrochemical, and material industries.

Publications

10 25 50

Studentship Projects

Project Reference Relationship Related To Start End Student Name
EP/N509486/1 01/10/2016 30/09/2021
1829120 Studentship EP/N509486/1 01/10/2016 30/09/2019 Alexander Williams
 
Description N-Methyliminodiacetic acid (MIDA) boronates are boronic acid derivatives which are stable to reduction, oxidation and transmetalation. This has led to their widespread use as boronic acid protecting groups (PGs) and in iterative cross-couplings. We describe herein the development of a novel MIDA derivative that acts in a dual manner, as a protecting group and a directing group (DG) for meta C(sp2)-H functionalisation of arylboronic acids. Palladium catalysed C-H alkenylations, acetoxylations and arylations are possible, at room temperature and under aerobic conditions. Deprotection to reveal the functionalised boronic acids is rapid and allows for full recovery of the DG. The technique allows the facile diversification of aryl boronic acids and their subsequent use in a range of reactions or in iterative processes.
Exploitation Route It may be used by chemists in industry or academia to access functionalised boronic acid building blocks for applications in fine chemicals or medicinal chemistry for example.
Sectors Chemicals,Pharmaceuticals and Medical Biotechnology

URL https://doi.org/10.1039/D0SC00230E