Phytic Acid-Modulated Ru Catalyzes Regioselective Deuteration of 1,6-Hexamethylenediamine

Regioselective deuteration is significant for the development of deuterated drugs and fine organic chemistry. However, the preparation of deuterated compounds by the hydrogen isotope exchange (HIE) reaction will generate a mixture of multiple isotopic isomers according to conventional catalysts. Therefore, it is significant to develop specific catalysts for regioselective deuteration. In this paper, phytate-captured Ru nanoparticles embedded within N-doped porous carbon were prepared for the synthesis of regioselective deuterated 1,6-hexamethylenediamine. The different chemical environments of Ru were constructed by oxygen and phosphorus functional groups in phytic acid to accomplish the fully deuterated 1,6-hexamethylenediamine and the selective 1,6-hexamethylenediamine α-H deuterated, respectively. Benefiting from its unique porous structure, which exposes a large number of active sites, it can exhibit HIE performance (both 94.4% D for all-H and 90.2% D for α-H) under mild conditions and using D2O as a deuterium source. The catalytic technology has enormous potential for the synthesis of a broad variety of deuterium-labeled compounds.