n-Butyllithium catalyzed hydroboration of imines and alkynes

The first examples of the hydroboration of imines with HBpin catalyzed by the commercially available n-BuLi are reported herein. Good functional group tolerance under mild conditions and short reaction time have been achieved. Further investigation showed that n-BuLi could also serve as an efficient catalyst for the hydroboration of alkynes with HBpin. High chemoselectivity toward imines over alkynes is presented. A possible mechanistic pathway of the n-BuLi catalyzed hydroboration of imines with HBpin is proposed based on computational studies.