B–N, B–O, and B–CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes

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• 作者：Rafal M. Dziedzic ; Liban M. A. Saleh ; Jonathan C. Axtell ; Joshua L. Martin ; Simone L. Stevens ; A. Timothy Royappa ; Arnold L. Rheingold ; Alexander M. Spokoyny
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：July 27, 2016
• 年：2016
• 卷：138
• 期：29
• 页码：9081-9084
• 全文大小：393K
• 年卷期：0
• ISSN：1520-5126

文摘

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.