Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines

A practical and efficient C(cage)–heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines. This reaction does not need the aid of any transition metal and utilizes readily available carboranyllithium nucleophiles, thereby avoiding transmetalation of carboranyllithium. The process exhibits a broad scope, and a vast array of 2-halopyridines have proven to be suitable substrates. The method serves as a complement to C(cage)–arylation reactions and may find wide applications in materials science and medicinal and coordination chemistry.