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

Abstract

AbstractThe 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 fluoropentafluorophenyl boryl radical causes generation of a 2‐difluoroboryl‐tetrafluorophenyl radical (B) via a second C−F bond activation. A perfluoroborepinyl radical (C) is also observed upon deposition and under UV‐Vis light irradiation. This finding reveals the new example of a dual C−F bond activation of hexafluorobenzene mediated by a nonmetal and provides a possible route for synthesis of new perfluorinated organo‐boron compounds.