Electrocatalytic hydrogenation of quinolines with water over a fluorine-modified cobalt catalyst

Shuoshuo Guo, Yongmeng Wu, Changhong Wang, Ying Gao, Mengyang Li, Bin Zhang () and Cuibo Liu ()
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Shuoshuo Guo: Tianjin University
Yongmeng Wu: Tianjin University
Changhong Wang: Tianjin University
Ying Gao: Tianjin University
Mengyang Li: Tianjin University
Bin Zhang: Tianjin University
Cuibo Liu: Tianjin University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: Abstract Room temperature and selective hydrogenation of quinolines to 1,2,3,4-tetrahydroquinolines using a safe and clean hydrogen donor catalyzed by cost-effective materials is significant yet challenging because of the difficult activation of quinolines and H2. Here, a fluorine-modified cobalt catalyst is synthesized via electroreduction of a Co(OH)F precursor that exhibits high activity for electrocatalytic hydrogenation of quinolines by using H2O as the hydrogen source to produce 1,2,3,4-tetrahydroquinolines with up to 99% selectivity and 94% isolated yield under ambient conditions. Fluorine surface-sites are shown to enhance the adsorption of quinolines and promote water activation to produce active atomic hydrogen (H*) by forming F−-K+(H2O)7 networks. A 1,4/2,3-addition pathway involving H* is proposed through combining experimental and theoretical results. Wide substrate scopes, scalable synthesis of bioactive precursors, facile preparation of deuterated analogues, and the paired synthesis of 1,2,3,4-tetrahydroquinoline and industrially important adiponitrile at a low voltage highlight the promising applications of this methodology.

Date: 2022
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DOI: 10.1038/s41467-022-32933-6

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