Hydrodenitrogenation of pyridines and quinolines at a multinuclear titanium hydride framework

Shaowei Hu, Gen Luo, Takanori Shima, Yi Luo () and Zhaomin Hou ()
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Shaowei Hu: RIKEN Center for Sustainable Resource Science and Organometallic Chemistry Laboratory
Gen Luo: RIKEN Center for Sustainable Resource Science and Organometallic Chemistry Laboratory
Takanori Shima: RIKEN Center for Sustainable Resource Science and Organometallic Chemistry Laboratory
Yi Luo: Dalian University of Technology
Zhaomin Hou: RIKEN Center for Sustainable Resource Science and Organometallic Chemistry Laboratory

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract Investigation of the hydrodenitrogenation (HDN) of aromatic N-heterocycles such as pyridines and quinolines at the molecular level is of fundamental interest and practical importance, as this transformation is essential in the industrial petroleum refining on solid catalysts. Here, we report the HDN of pyridines and quinolines by a molecular trinuclear titanium polyhydride complex. Experimental and computational studies reveal that the denitrogenation of a pyridine or quinoline ring is easier than the ring-opening reaction at the trinuclear titanium hydride framework, which is in sharp contrast with what has been reported previously. Hydrolysis of the pyridine-derived nitrogen-free hydrocarbon skeleton at the titanium framework with H2O leads to recyclization to afford cyclopentadiene with the generation of ammonia, while treatment with HCl gives the corresponding linear hydrocarbon products and ammonium chloride. This work has provides insights into the mechanistic aspects of the hydrodenitrogenation of an aromatic N-heterocycle at the molecular level.

Date: 2017
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DOI: 10.1038/s41467-017-01607-z

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