Carbodiphosphorane-Catalyzed Hydroboration of Ketones and Imines

Abstract

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