3 years ago

On the Reactivity of the Carba-closo-dodecaborate Anion with the Trityl Cation

On the Reactivity of the Carba-closo-dodecaborate Anion with the Trityl Cation
Steven P. Fisher, Vincent Lavallo, Jack F. Kleinsasser, Fook S. Tham
In 1994 Reed and co-workers reported a variety of trityl salts with various functionalized icosahedral carborane anions. However, it was mentioned that the parent carba-closo-dodecaborate anion [HCB11H11]– underwent an unidentified chemical reaction with the trityl cation as the ion pair formed in solution. In this communication, we have reexamined this reaction and identified the reaction as classical electrophilic substitution of a carborane B–H bond to afford new B-arylated compounds, and not a carborane dimer as previously proposed. This is the first example of the electrophilic arylation of the [HCB11H11]– anion. The new arylated carborane anions are fully characterized by multinuclear NMR and IR spectroscopy, as well as single-crystal X-ray diffraction studies.It was previously reported that the carba-closo-dodecaborate anion [HCB11H111–] is incompatible with the trityl cation, but no products were unambiguously identified from the reaction. In this communication we reinvestigate this reaction and identify it as the first example of the electrophilic arylation of a closo-carborane anion.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejic.201700614

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