Development of palladium-catalyzed cross-coupling reactions for the CB₁₁⁻ carborane

Previous work in the Juhasz Lab had explored the palladium catalyzed Kumada coupling as a method to functionalize the 1-carba-closo-dodecaborate(-) anion (also known as CB₁₁⁻) at the 12-boron vertex. In this presented research, several other palladium catalyzed reactions were tested to varying degrees of success. A Suzuki-style coupling with arylboronic acids failed to produce any desired product. A Heck-type coupling had high turnover of starting material into desired product but with moderate quantities of inseparable byproducts. A novel reaction that used a palladium catalyst and silver acetate to put an acetyl group on the cluster was also discovered and explored. These findings offer new insights to the reactivity of the CB₁₁⁻ cluster and future strategies for synthesizing derivatives.