Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Cage-Walking: Vertex Differentiation by Palladium-Catalyzed Isomerization of B(9)-Bromo-meta-Carborane

Cage-Walking: Vertex Differentiation by Palladium-Catalyzed Isomerization of B(9)-Bromo-meta-Carborane
Jonathan C. Axtell, Arnold L. Rheingold, Liban M. A. Saleh, K. N. Houk, Joshua L. Martin, Rafal M. Dziedzic, Marco S. Messina, Ta-Chung Ong, Alexander M. Spokoyny, Yun-Fang Yang
We report the first observed Pd-catalyzed isomerization (“cage-walking”) of B(9)-bromo-meta-carborane during Pd-catalyzed cross-coupling, which enables the formation of B–O and B–N bonds at all boron vertices (B(2), B(4), B(5), and B(9)) of meta-carborane. Experimental and theoretical studies suggest this isomerization mechanism is strongly influenced by the steric crowding at the Pd catalyst by either a biaryl phosphine ligand and/or substrate. Ultimately, this “cage-walking” process provides a unique pathway to preferentially introduce functional groups at the B(2) vertex using B(9)-bromo-meta-carborane as the sole starting material through substrate control.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04080

DOI: 10.1021/jacs.7b04080

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