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March 26, 2026Journal of the American Chemical Society4 citations

Cobalt-Catalyzed Highly Enantioselective Hydrogenation of Quinolines under Mild Conditions

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MZMengya ZhangLLLin LiuCWChao Wang

Key Points

  • The objective is to develop a cobalt pincer complex for asymmetric hydrogenation of quinolines to achieve high enantioselectivity.
  • Synthesis of a cobalt pincer complex with PNN ligand
  • Application of the catalyst in asymmetric hydrogenation of quinolines
  • Use of probe reactions and DFT calculations to investigate reaction pathway
  • Hydrogenation of quinolines resulted in chiral 1,2,3,4-tetrahydroquinolines with yields close to 100%
  • Achieved enantioselectivities up to 99.9% ee across 51 examples
  • DFT calculations suggest a stepwise 1,2–1,2-hydride transfer pathway

Abstract

A cobalt pincer complex has been designed, synthesized, and successfully applied to catalytic asymmetric hydrogenation of quinolines under mild conditions. Containing a PNN ligand that features both a P and a C-stereogenic center, the cobalt catalyst allows for the hydrogenation of a variety of quinolines to afford chiral 1,2,3,4-tetrahydroquinolines with high yields and excellent enantioselectivities in general (51 examples, up to 99.9% ee). Probe reactions and DFT calculations suggest that the hydrogenation proceeds via a stepwise 1,2–1,2-hydride transfer pathway. The results obtained could provide a valuable hint for the development of more efficient 3d transition metal catalysts for asymmetric catalysis.

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/69c4ccf7fdc3bde448918b3fhttps://doi.org/10.1021/jacs.6c01182
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