In 2008, the Ozerov group reported catalytic hydrodefluorination (HDF) of various organic compounds which contain C(sp3)-F bonds under mild conditions.[1] The keys to a successful reaction were fluorophilic silylium cations generated in situ by reacting trityl cations with silanes. However, activation of C(sp3)-F bonds in perfluoroalkanes still remains a challenge. HDF of perfluoroalkanes would require trityl cations with higher hydride affinity to generate more fluorophilic silylium cations.[2] Based on this concept, trityl salts with strong electron-withdrawing substituents (eg. m-fluoro) of carborane anions were synthesized and tested in HDF. Meanwhile, utilization of these trityl cations in generating new main group and transition metal cations by abstraction and/or oxidation will also be discussed in this presentation.[1] Douvris, C.; Ozerov, O. V Science 2008, 321, 1188[2] Gusev, D. G.; Ozerov, O. V. Chem. Eur. J. 2011, 17, 634

Synthesis and reactivity of highly electrophilic trityl salts of carborane anions

247th National Meeting (2014)

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