Introducing Frustrated Lewis Pairs to Metal–Organic Framework for Selective Hydrogenation of N‑Heterocycles

• Published in: Journal of the American Chemical Society Vol. 145; no. 27; pp. 14994 - 15000
• Main Authors: Xu, Ze-Ming, Hu, Zhuoyi, Huang, Yali, Bao, Shu-Jin, Niu, Zheng, Lang, Jian-Ping, Al-Enizi, Abdullah M., Nafady, Ayman, Ma, Shengqian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.07.2023; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; HETEROARENES; DESIGN; MILD CONDITIONS; ETHYLENE; REDUCTION; LIGANDS; CONVERSION; CATALYTIC-HYDROGENATION; CENTERS; SOLVENT
• DOI: 10.1021/jacs.3c04929
• ISSN: 0002-7863

Hydrogenated nitrogen heterocyclic compounds play a critical role in the pharmaceutical, polymer, and agrochemical industries. Recent studies on partial hydrogenation of nitrogen heterocyclic compounds have focused on costly and toxic precious metal catalysts. As an important class of main-group catalysts, frustrated Lewis pairs (FLPs) have been widely applied in catalytic hydrogenation reactions. In principle, the combination of FLPs and metal–organic framework (MOF) is anticipated to efficiently enhance the recyclability performance of FLPs; however, the previously studied MOF-FLPs showed low reactivity in the hydrogenation of N-heterocycles compounds. Herein, we offer a novel P/B type MOF-FLP catalyst that was achieved via a solvent-assisted linker incorporation approach to boost catalytic hydrogenation reactions. Using hydrogen gas under moderate pressure, the proposed P/B type MOF-FLP can serve as a highly efficient heterogeneous catalyst for selective hydrogenation of quinoline and indole to tetrahydroquinoline and indoline-type drug compounds in high yield and excellent recyclability.