Phytic Acid-Modulated Ru Catalyzes Regioselective Deuteration of 1,6-Hexamethylenediamine
Fangjun Shao, Kui Wang, Wenjie Jiang, Zhanpeng Xu, Xiaolong Li, Xing Zhong, Jianguo Wang
Abstract
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 D 2 O as a deuterium source. The catalytic technology has enormous potential for the synthesis of a broad variety of deuterium-labeled compounds.