Electrooxidative B-H Functionalization of nido-Carboranes

An atom-economical method for the direct B-H functionalization of nido-carboranes (7,8-nido-C2B9H12-) has been developed under electrochemical reaction conditions. In this reaction system, anodic oxidation serves as a green alternative for traditional chemical oxidants in the oxidation of nido-carboranes. No transition-metal catalyst is required and different heteroatoms bearing a lone pair are reactive in this transformation. Coupling nido-carboranes with thioethers, selenides, tellurides, N-heterocycles, phosphates, phosphines, arsenides and antimonides demonstrates high site-selectivity and efficiency. Importantly, nido-carboranes can be easily incorporated into drug motifs through this reaction protocol.

Automated summary

An atom-economical method has been developed for the direct B-H functionalization of nido-carboranes under electrochemical reaction conditions, without the need for transition-metal catalysts. The reaction demonstrates high site-selectivity and efficiency, and allows for easy incorporation of nido-carboranes into drug motifs.