Long-Range C–H Bond Activation by Rh^(III)-Carboxylates
Matthew E. O'Reilly, Ross Fu, Robert J. Nielsen, Michal Sabat, William A. Goddard III, T. Brent Gunnoe
2014J. Am. Chem. Soc., 136(42), 14690-1469328cited
Abstract
Traditional C–H bond activation by a concerted metalation–deprotonation (CMD) mechanism involves precoordination of the C–H bond followed by deprotonation from an internal base. Reported herein is a "through-arene" activation of an uncoordinated benzylic C–H bond that is 6 bonds away from a Rh^(III) ion. The mechanism, which was investigated by experimental and DFT studies, proceeds through a dearomatized xylene intermediate. This intermediate was observed spectroscopically upon addition of a pyridine base to provide a thermodynamic trap.
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O'Reilly, M. E., Fu, R., Nielsen, R. J., Sabat, M., III, W. A. G., & Gunnoe, T. B. (2014). Long-Range C–H Bond Activation by Rh^(III)-Carboxylates. *J. Am. Chem. Soc.*, *136*(42), 14690-14693. https://doi.org/10.1021/ja508367m