Zaozao Qiu shows in this thesis that transition metals can mediate or catalyze the cycloaddition or coupling reactions of carboryne with alkynes or alkenes to afford benzocarboranes, alkenylcarboranes or dihydrobenzocarboranes. These results represent powerful strategies to assemble useful complex molecules from very simple precursors in a single operation. Carboranes have many applications in medicine. However, their unique structures make derivatization difficult and the limited efficient synthetic methods to obtain functional carborane materials have restricted applications of carboranes within a narrow scope. This work breaks a new ground in metal-carboryne chemistry and will have a significant impact on synthetic, cluster and materials chemistry.

Introduction

Nickel-1,2-o-Carboryne Complexes
Nickel-Mediated Coupling Reactions of 1,2-o-Carboryne with Alkenes
Nickel-Mediated/Catalyzed Three-Component Cycloaddition Reaction of 1,2-o-Carboryne/Arynes, Alkenes, and Alkynes
Nickel-Catalyzed Regioselective [2+2+2] Cycloaddition of 1,2-o-Carboryne with Alkynes
Palladium/Nickel-Cocatalyzed [2+2+2] Cycloaddition of 1,3-o-Carboryne with Alkynes
Conclusion
Experimental Section.