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Oxidative Generation of Boron-Centered Radicals in Carboranes

preprint
submitted on 22.12.2019 and posted on 23.12.2019 by Harrison A. Mills, Joshua Martin, Arnold L. Rheingold, Alexander Spokoyny

We report the first indirect observation and use of boron vertex-centered carboranyl radicals generated by the oxidation of modified carboranyl precursors. These radical intermediates are formed by the direct oxidation of a B−B bond between a boron cluster cage and an exopolyhedral boron-based substituent (e.g., −BF3K, −B(OH)2). The in situ generated radical species are shown to be competent substrates in reactions with oxygen-based radicals, dichalcogenides, and N-heterocycles, yielding the corresponding substituted carboranes containing B−O, B−S, B−Se, B−Te, and B−C bonds. Remarkably, this chemistry tolerates various electronic environments, providing access to facile substitution chemistry at both electron-rich and electron-poor B−H vertices in carboranes.

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in Journal of the American Chemical Society

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Funding

NIGMS R35GM124746

History

Email Address of Submitting Author

spokoyny@chem.ucla.edu

Institution

UCLA

Country

USA

ORCID For Submitting Author

0000-0002-5683-6240

Declaration of Conflict of Interest

Authors declare no conflicts of interest.

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Read the published paper

in Journal of the American Chemical Society

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