Expanding the Scope of Palladium-Catalyzed B–N Cross-Coupling Chemistry in Carboranes

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Abstract
Over the past several years, a number of strategies for the functionalization of dicarba-closo-dodecaboranes (carboranes) have emerged. Despite these developments, B–N bond formation on the carborane scaffold remains a challenge due to the propensity of strong nucleophiles to partially deboronate the parent closo-carborane cluster into the corresponding nido form. Here we show that azide, sulfonamide, cyanate, and phosphoramidate nucleophiles can be straightforwardly cross-coupled onto the B(9) vertices of the o- and m-carborane core from readily accessible precursors without significant deboronation byproducts, laying the groundwork for further study into the utility and properties of these new B-aminated carborane species. We further showcase the select reactivity of the installed functional groups, highlighting some unique features stemming from the combination of the electron-donating B(9) position and the large steric profile of the B-connected carborane substituent.
Funding Information
  • Camille and Henry Dreyfus Foundation
  • National Institute of General Medical Sciences (1DP2GM13268, R35GM124746)

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