Carbodiphosphorane-Catalyzed Hydroboration of Ketones and Imines

We report the use of a cyclic carbodiphosphorane catalyst for ketone and imine hydroboration reactions. Ketone reactions are particularly rapid, typically reaching completion within 15 min using 1 mol % loading at 25 °C. To our knowledge, this represents first as an organocatalyst. The exhibited superior catalytic activity in comparison to other neutral carbon nucleophiles tested, including N-heterocyclic carbene, olefin, phosphorus ylides.