An anthranilamide-substituted borane [H-B(aam)]: its stability and application to iridium-catalyzed stereoselective hydroboration of alkynes.

A new anthranilamide-substituted borane [H-B(aam)] was synthesized and found to serve as a stable, easy-to-handle substitute for H-B(pin). It was applied to the direct synthesis of diverse linear (E)-alkenyl-B(aam)s via regio- and stereoselective hydroboration of terminal alkynes under iridium catalysis. A boryliridium hydride complex arising from the oxidative addition of H-B(aam) to the Ir catalyst was isolated and characterized via NMR studies.