B–N, B–O, and B–CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes
- 13 July 2016
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 138 (29), 9081-9084
- https://doi.org/10.1021/jacs.6b05505
Abstract
Carboranes are boron-rich molecules that can be functionalized through metal-catalyzed cross-coupling. Here, for the first time, we report the use of bromo-carboranes in palladium-catalyzed cross-coupling for efficient B-N, B-O, and unprecedented B-CN bond formation. In many cases bromo-carboranes outperform the traditionally utilized iodo-carborane species. This marked difference in reactivity is leveraged to circumvent multistep functionalization by directly coupling small nucleophiles (-OH, -NH2, and -CN) and multiple functional groups onto the boron-rich clusters.Funding Information
- Division of Chemistry (CHE-1048804)
- 3M
- Department of Chemistry and Biochemistry, University of California, Los Angeles
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