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.