Issue 45, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
30 avq 2019
Accepted
10 okt 2019
First published
11 okt 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 10459-10465

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

Y. Wu, H. Yu, Y. Guo, X. Jiang, Y. Qi, B. Sun, H. Li, J. Zheng and X. Li, Chem. Sci., 2019, 10, 10459 DOI: 10.1039/C9SC04365A

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