Photoinduced Dual C-F Bond Activation of Hexafluorobenzene Mediated by Boron Atom.

The reaction of laser-ablated boron atoms with hexafluorobenzene (C6F6) was investigated in neon and argon matrices, and the products are identified by matrix-isolation infrared spectroscopy and quantum-chemical calculations. The reaction is triggered by a boron atom insertion into one C-F bond of hexafluorobenzene on annealing, forming a fluoropentafluorophenyl boryl radical (A). UV-Vis light irradiation of the  fluoropentafluorophenyl boryl radical causes generation of a 2-difluoroboryl-tetrafluorophenyl radical (B) via a second C-F bond activation. A perfluoroborepinyl radical (C) generated from the C-C bond insertion reaction is also observed upon deposition and under UV-Vis light irradiation. These findings reveal the first example of a double C-F bond activation of hexafluorobenzene mediated by a nonmetal and provides a possible route for synthesis of new perfluorinated organo-boron compounds.

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