The 1-carba-closo-dodecaborate(1-) carborane anion (closo-CB11-), has potential uses in medicine, as a non-interfering counter-anion for cationic catalysts, and in optical and electronic materials, but relatively few synthetic methods exist for preparing useful derivatives of this cluster. In an effort to expand the synthetic repertoire of closo-CB11-, we have developed a copper-promoted cross-coupling method for cyanating boron vertices of this anion. Clusters with one or two cyano groups can be prepared efficiently by this strategy: 12-CN-CHB11H10- and 7,12-(CN)2-CHB11H9- were each synthesized in yields of over 80%. These anions are the first examples of boron-cyanated derivatives of closo-CB11-, and their salts were fully characterized by NMR, IR, MS, and X-ray crystallography. The CN group is synthetically versatile and its attachment to the closo-CB11- cluster opens the door to a variety of new derivatives. The cyanation method and subsequent reactivity of cyanated closo-CB11- derivatives will be discussed.

Copper-promoted cyanation of the closo-CB11- cluster: Synthesis and reactivity of 12-CN-closo-CHB11H10� and 7,12-(CN)2-closo-CHB11H9-

247th National Meeting (2014)

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