Electrophilic borylation improves reactivity of nonactivated arenes with pyramidal boron superacids, suggesting new pathways for aromatic transformations.
The electrophilic C–H borylation of unactivated and deactivated, electron-poor arenes is a challenging reaction even with the most electrophilic borenium-ion species. We now report the transition-metal-free borylation of a wide range of aromatics and polyaromatics with a pyramidal boron Lewis superacid from the 9-boratriptycene family. The mechanism of formation of a highly reactive pyramidal boron Lewis superacid and the origin of the slow and continuous release of this highly reactive borylation reagent in the presence of a Lewis base are reminiscent of the reactions of latent frustrated Lewis pairs with small molecules.
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Osi et al. (2025) studied this question.
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