Palladium catalyzed selective arylation of o-carboranes via B(4)–H activation: amide induced regioselectivity reversal.

By changing the charge distribution of boron vertices via introducing an amide on cage B(9), the selective B(4) arylation of o-carboranes via Suzuki–Miyaura coupling has been developed. A series of o-carborane derivatives decorated with diverse active groups have been synthesized with moderate to good yields, which have been proved to be further transformed to a novel kind of tri-substituted nido-carborane fused oxazole with potential application in boron neutron capture therapy, organometallic as well as coordination chemistry. [ABSTRACT FROM AUTHOR]