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November 30, 2025Chemistry - An Asian Journal2 citations

A Mixed‐Carbene‐Donor Strategy for Co(III)‐Catalyzed Selective Reduction of Quinolines

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ADAditya DeyMSMisba SiddiqueARARNAB RIT

Key Points

  • Selective hydrogenation of quinoline derivatives significantly enhances their potential for pharmaceuticals and bioactive molecules.
  • The method achieves efficient transfer hydrogenation without additives, providing excellent selectivity to diverse functional groups.
  • Utilization of a mixed-NHC-based Co(III) catalyst promotes partial hydrogenation of quinoline scaffolds, enhancing drug development options.
  • Mechanistic studies indicate the cobalt-hydride intermediate is active, with enhanced hydride donor capability from the carbene environment.

Abstract

Abstract The selective hydrogenation of aromatic N‐heterocycles is an important transformation in synthetic chemistry, as the resulting partially saturated derivatives are widely found in pharmaceuticals and bioactive molecules. In this context, quinolines are especially important, with 1,2,3,4‐tetrahydroquinolines serving as the privileged scaffolds in various drugs. To achieve such selective hydrogenation, we herein describe the synthesis and characterization of a series of NHC‐derived heteroditopic bidentate ligands, including a combination of imidazole‐based N‐heterocyclic carbene (ImNHC) with a triazole‐derived “mesoionic” NHC (TzNHC) donor, supported by well‐defined Co(III)‐complexes. Among them, the mixed‐NHC‐based Co(III) catalyst enables efficient, additive‐free transfer hydrogenation (TH) of diverse quinoline derivatives with excellent selectivity and tolerance to diverse functional groups. Mechanistic studies indicate that a cobalt‐hydride intermediate is the active species, with the mixed donor carbene environment enhancing the hydride donor capability, enabling selective reduction.

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Cite This Study

Dey et al. (2025) studied this question.

synapsesocial.com/papers/692b9da01d383f2b2a37a37ehttps://doi.org/10.1002/asia.202500927
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