960化工网
A rare earth hydride supported ruthenium catalyst for the hydrogenation of N-heterocycles: boosting the activity via a new hydrogen transfer path and controlling the stereoselectivity†
Yong Wu,Hongen Yu,Yanru Guo,Xiaojing Jiang,Yue Qi,Bingxue Sun,Haiwen Li,Jie Zheng,Xingguo Li
Chemical Science Pub Date : 10/11/2019 00:00:00 , DOI:10.1039/C9SC04365A
Abstract

Hydrogenation of N-heterocycles is of great significance for their wide range of applications such as building blocks in drug and agrochemical syntheses and liquid organic hydrogen carriers (LOHCs). Pursuing a better hydrogenation performance and stereoselectivity, we successfully developed a rare earth hydride supported ruthenium catalyst Ru/YH3 for the hydrogenation of N-heterocycles, especially N-ethylcarbazole (NEC), the most promising LOHC. Full hydrogenation of NEC on Ru/YH3 can be achieved at 363 K and 1 MPa hydrogen pressure, which is currently the lowest compared to previous reported catalysts. Furthermore, Ru/YH3 shows the highest turnover number, namely the highest catalytic activity among the existing catalysts for hydrogenation of NEC. Most importantly, Ru/YH3 shows remarkable stereoselectivity for all-cis products, which is very favorable for the subsequent dehydrogenation. The excellent performance of Ru/YH3 originates from the new hydrogen transfer path from H2 to NEC via YH3. Ru/LaH3 and Ru/GdH3 also reveal good activity for hydrogenation of NEC and Ru/YH3 also possesses good activity for hydrogenation of 2-methylindole, indicating that the use of rare earth hydride supported catalysts is a highly effective strategy for developing better hydrogenation catalysts for N-heterocycles.

Graphical abstract: A rare earth hydride supported ruthenium catalyst for the hydrogenation of N-heterocycles: boosting the activity via a new hydrogen transfer path and controlling the stereoselectivity
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