meta-Selective C–H Arylation of Phenols via Regiodiversion of Electrophilic Aromatic Substitution
Liam Ball used a regiodiversion of electrophilic aromatic substitution for the C–H arylation of phenols.
The meta-selective C–H arylation of phenols is an enduring challenge in organic synthesis. Not only is the meta position deactivated towards electrophilic substitution – the most common reaction manifold for phenols – but it is also beyond the reach of most directing groups that could be appended to the phenolic oxygen. Although this challenge has attracted several pioneering solutions based on Pd-catalyzed C–H functionalization, these methods do not tolerate an existing ortho substituent on the phenol. As such, phenols featuring contiguous substitution patterns remain severely underrepresented in chemical libraries. Dr. Liam Ball and his team at the University of Nottingham (UK) recognized that they could potentially address this limitation using a fundamentally different reaction manifold: Bi(V)-mediated electrophilic arylation.