Sodium as High-efficient Catalyst in Hydroboration of Unsaturated Compounds

The catalysts used to catalyze the hydroboration of nitriles or carbodiimides usually have some disadvantages such as complex structure, high cost, large pollution of environment and so on. It is an important development direction to use the main group metals instead of the transition metals to reduce the costs and realize green catalysis. In this paper, using NaH or NaOH as a catalyst, an efficient reaction of nitrile or carbodiimide with pinacol borane (HBPin) has been achieved. It was found that 3.5 mol% of NaH participated in the hydroboration reaction in a simple and effective method under slight solvent-free circumstances. In addition, intermolecular chemoselectivity hydroboration of nitrile and substrates with different functional groups was also investigated by employing three different catalysts. This reaction uses the inorganic alkali with simple structure, commercially available and low cost to synthesize organoborane compounds, which provides ideas for industrial development.