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An efficient and succinct protocol for synthesis of bis(o-carborane) connected by a B−B bond via palladium catalyzed oxidative dehydrogenative coupling of cage B−H/B−H bonds was developed for the first time. A series of bis(ocarborane)s connected by B(4)−B(4)′ and B(4)−B(5)′ bonds was synthesized with moderate to good yields. This work opens the door for miscellaneous applications of bis(o-carborane) in related disciplines and has important value in design and synthesis of different kinds of biscarboranes.

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A palladium catalyzed selective B(3)–H activation/oxidative dehydrogenative coupling for the synthesis of bis­(o-carborane)­s connected with B(3)–B(3′) and B(3)–B(6′) bonds has been developed for the first time. A plausible mechanism involving stepwise activation of B(3)–H and B­(3′/6′)–H bonds by PdII and PdIV was proposed. This work is the first example and the most efficient protocol for synthesis of bis­(o-carborane)­s connected with B(3)–B(3′) and B(3)–B(6′) bonds, which has important reference for design, synthesis, and application of bis­(o-carborane)­s in related fields.

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A palladium catalyzed/silver tuned selective mono- and tetra-acetoxylation of o-carboranes has been developed, and a series of mono- and tetra-acetoxylated o-carboranes decorated with active groups have been synthesized with moderate to good yields as well as excellent selectivity. A mechanism involving electrophilic palladation and cyclopalladation of the B-H bond was proposed.

An efficient in situ Pd-NHC catalytic system for regioselective arylation of B­(3,6)–H bonds of o-carborane has been developed for the first time. A series of symmetric and unsymmetric 3,6-diaryl-o-carboranes anchored with active groups have been synthesized with moderate to good yields under mild conditions. This work offers an efficient protocol for selective activation of B­(3,6)–H bonds and has important value in design coupling reactions for selective functionalization of o-carboranes.