C-H Functionalization of BN-Aromatics Promoted by Addition of Organolithium Compounds to the Boron Atom.

Addition of an organolithium compound to a BN-phenanthrene with embedded B and N atoms is proposed to result in coordination of RLi to the boron atom. This coordination, supported by NMR spectroscopy and DFT calculations, increases the nucleophilicity of the system in the β position to the N atom and is therefore a useful tool for promoting regioselective C-H functionalization of BN aromatics.