Hydrolysis of B2pin2 over Pd/C Catalyst: High Efficiency, Mechanism, and in situ Tandem Reaction

A facile and effective synthesis of H-2 or D-2 from Pd/C catalyzed hydrolysis of B(2)pin(2) has first been developed. Among them, B(2)pin(2) is frequently used for borylation reaction, and has rarely been used for hydrogen evolution. The kinetic isotope effects (KIEs) and tandem reaction for diphenylacetylene and norbornene hydrogenation have confirmed both two H atoms of H-2 gas are provided from H2O. This is contrary to other boron compounds hydrolysis (including NH3BH3, NaBH4), which generates H-2 with only one H atom provided by water and the other one by boron compounds. Note that the hydrolysis of B(2)pin(2) in D2O also provides an easy and useful synthesis of D-2.

Automated summary

A facile and effective method for synthesizing H-2 or D-2 from Pd/C catalyzed hydrolysis of B(2)pin(2) has been developed. The kinetic isotope effects (KIEs) and tandem reaction confirmed that both hydrogen atoms in H-2 gas are provided by H2O. Also, the hydrolysis of B(2)pin(2) in D2O provides an easy synthesis of D-2.