Recent Progress in the Synthesis of the Monocarba-closo-dodecaborate(−) Anions

This Concept article focuses on the rapid growth in studies of the chemistry of the monocarba-closo-dodecaborate(−) anion (C1 carborane anion). As one of the most stable anions known, the C1 carborane anion has been useful for exploring the chemistry of highly reactive cations. On the other hand, development of novel functional molecules utilizing the unique properties of C1 carborane anion (e.g., σ-aromaticity, rigid spherical skeleton) has progressed more slowly. The main reason for this is the relatively undeveloped state of synthetic chemistry in this area. Recent advances in the synthetic chemistry of C1 carborane anion are highlighted in this Concept article, focusing on cross-coupling reactions at the carbon vertex, direct conversion of B−H bonds, and the synthesis of multivalent weakly coordinating anions. These progressions move this species beyond its well-established role of highly stable “counter” monocharged anion.