Pd-Catalyzed Oxidative Dehydrogenative Cross Coupling of Cage B–H/B–H Bonds at Room Temperature: Synthesis of Bis(o-carborane)s

Abstract

Efficient Pd-catalyzed oxidative dehydrogenative cross coupling of B–H/B–H bonds of two pyridyl o-carboranes has been developed, leading to the preparation of B(3)–B(6′) heterocoupled and B(3)–B(6′) homocoupled biscarboranes with a broad substrate scope at room temperature.

9,9′-Bis-o-carboranes: synthesis and exploration of properties

“…Recently, Pd( ii )-catalyzed dehydrogenative B–H/B–H coupling with a directing group was established (Scheme 1d). 21 From the viewpoint of practicability, the direct B–H/B–H oxidative dehydrogenation coupling of carboranes to bis(carborane) without a directing group is more attractive as it has wide applications in organic syntheses. Herein, we developed a palladium-catalyzed direct oxidative dehydrogenation coupling of o -carboranes to synthesize 9,9′-bis- o -carboranes with >99 : 1 B(9) selectivity.…”