Cesium carbonate mediated C-H functionalization of perhalogenated 12-vertex carborane anions.

C-H functionalization of undecahalogenated carborane anions, [HCBX] (X = Cl, Br, I), is performed with CsCO in acetonitrile. We show that the requisite Cl, Br and I carborane dianions can all be efficiently accessed with CsCO. The utilization of CsCO eliminates the complications associated with competing E2 elimination reactions providing an efficient, more functional group tolerant, and broader scope than previously reported.