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Chemoselective Transfer Hydrogenation of Nitroarenes with Ammonia Borane Catalyzed by Copper N-heterocyclic Carbene Complexes
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  • Hui Zhou,
  • Hongmei Jiao,
  • Xing Lu,
  • Yuanyuan Gao,
  • Zhiqiang Ren,
  • Haojie Ma,
  • Yuqi Zhang,
  • Bo Han
Hui Zhou
Yan'an University
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Hongmei Jiao
Yan'an University
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Xing Lu
Yan'an University
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Yuanyuan Gao
Yan'an University
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Zhiqiang Ren
Yan'an University
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Haojie Ma
Yan'an University
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Yuqi Zhang
Yan'an University
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Bo Han
Yan'an University

Corresponding Author:[email protected]

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Abstract

Herein, we present a method for the homogeneous hydrogenation of nitroarenes to produce aromatic amines using low catalyst loading (1 mo%) of air-stable copper N-heterocyclic carbene complexes as the catalyst and ammonia borane as the source of hydrogen. A wide range of nitroarenes, featuring diverse functional groups, were selectively transformed into their corresponding primary aromatic amines with high yields. This process can be readily scaled up and exhibits compatibility with various sensitive functional groups, including halogen, trifluoromethyl, aminomethyl, alkenyl, cyano, ester, amide, and hydroxyl. Notably, this catalytic methodology finds application in the synthesis of essential drug compounds. Mechanistic investigations suggest that the in-situ-generated Cu-H species may serve as active intermediates, with reduction pathways involving species such as azobenzene, 1,2-diphenylhydrazine, nitrosobenzene, and N-phenylhydroxylamine.
25 Jan 2024Assigned to Editor
25 Jan 2024Submission Checks Completed
25 Jan 2024Review(s) Completed, Editorial Evaluation Pending
30 Jan 2024Reviewer(s) Assigned