Electrooxidative B-H Functionalization of nido-Carboranes.

An atom-economical method for the direct B-H functionalization of nido-carboranes (7,8-nido-C2 B9 H12 - ) 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.