The Development of Novel Ligands to Target the Para-Selective Borylation of a Range of Aromatic Compounds

Lead Research Organisation: University of Cambridge
Department Name: Chemistry

Abstract

The iridium-catalysed conversion of aromatic C-H bonds to boronate esters is one of the most efficient and versatile methods for building complex aromatic rings. We have recently demonstrated a novel anionic ligand-cationic substrate approach to achieving elusive meta selectivity in the borylation of several classes of aromatic ammonium salts. The key aim of this project will be to design new ligand scaffolds to target the para position of substituted arenes for borylation. There are very few methods for para-selective C-H functionalisation using transition metals and our approach offers an ideal opportunity to address this. We envisage that the ligands developed will also be applied to para-selective borylation of other substrates such as aromatic amides, through hydrogen bonding interactions, which we are developing in parallel in our lab.

Publications

10 25 50

Studentship Projects

Project Reference Relationship Related To Start End Student Name
EP/N509620/1 01/10/2016 30/09/2022
1800481 Studentship EP/N509620/1 01/10/2016 31/03/2020 James Douthwaite
 
Description The work this award has funded has moved away from para-selective borylation into the field of enantioselective borylation - a challenge at the very cutting edge of transition metal catalysis. We have utilized a novel strategy which has allowed us to apply chiral cations to transition metal catalysis, to do enantioselective borylation. This is a potentially significant advancement as many chiral cations are readily available privileged structures which have proven themselves time and again to be good chiral controllers in organocatalysis. We hope that our strategy of incorporating them into transition metal catalysis will be generally applicable to other transformations, opening the door to new asymmetric reactions. The significance of this advancement is reflected in the work being accepted into the journal Science, and is due for online publication on the 12th March
Exploitation Route The outcome of the recent work described above could have a significant implication in helping synthetic chemists develop new and improved asymmetric transition metal catalysed reactions. This is turn may allow easier access to bioactive compounds which are sought after by the phrama/agrochemical industries etc., allowing them to create new medicines/pesticides etc.
Sectors Chemicals,Pharmaceuticals and Medical Biotechnology