B–N, B–O, and B–CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes
| Autor: | Arnold L. Rheingold, A. Timothy Royappa, Liban M. A. Saleh, Joshua L. Martin, Jonathan C. Axtell, Alexander M. Spokoyny, Rafal M. Dziedzic, Simone L. Stevens |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry chemistry.chemical_element General Chemistry Bond formation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Catalysis 0104 chemical sciences Coupling (electronics) Colloid and Surface Chemistry Nucleophile Organic chemistry Surface modification Molecule Reactivity (chemistry) Palladium |
| Zdroj: | Journal of the American Chemical Society. 138:9081-9084 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.6b05505 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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