The direct, selective conversion of ubiquitous C–H bonds in to synthetically versatile C–B bonds is attractive in organic synthetic and potentially enabling in green chemistry as synthetic steps are potentially eliminated. Our laboratory has discovered a class of cobalt catalysts supported by various tridentate pincer ligands that promote the borylation of C(sp2)–H bonds. With fluorinated arenes, control over ortho, meta and para selectivity has been achieved. The various catalyst types operate in distinct kinetic regimes and the observed selectivity derives from whether the C–H bond breaking step is under kinetic or thermodynamic control. Importantly, the observed reactivity and selectivity dervies from inherent electronic differences in the C–H bonds rather than from more traditional (and limited) directing group strategies. The various kinetic regimes and how the properties of the supporting ligands enable the selectivity of the reaction will be discussed as well applications to important synthetic intermediates.

Cobalt catalyzed C–H borylation: Unprecedented selectivity opens pathway to greener organic synthesis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.