Cobalt single-atom catalysts for domino reductive amination and amidation of levulinic acid and related molecules to N-heterocycles

Jie Gao, Lu Feng, Rui Ma, Bing Jian Su, Asma M. Alenad, Yuefeng Liu, Matthias Beller, Rajenahally V. Jagadeesh

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

The development of single-atom-based catalysts (SACs), which bridge the traditional areas of homogeneous and heterogeneous catalysis, continues to be important for achieving organic synthesis in a more efficient and practical manner. Here, we report reusable cobalt-based SACs for the selective and general reductive amination of levulinic acid and related keto acids, which is of interest in the context of valorization of biomass. The optimal Co-SAC-based catalyst is prepared by pyrolysis (800°C) of cobalt-phenanthroline complexe on carbon and subsequent acid treatment. The resulting Co-SACs showed amazing activity compared with the corresponding Co-nanoparticles and displayed an excellent substrate scope for various reductive domino transformations including reactions of levulinic acid with nitro compounds and nitriles to produce various N-substituted pyrrolidones in good to excellent yields. Further, the synthesis of diverse isoindolinones from aromatic ketoacids and amines/nitro compounds was performed with the optimal catalyst system.

Original languageEnglish
Pages (from-to)178-194
Number of pages17
JournalChem Catalysis
Volume2
Issue number1
DOIs
StatePublished - 20 Jan 2022
Externally publishedYes

Keywords

  • N-heterocycles
  • SDG3: Good health and well-being
  • SDG9: Industry innovation and infrastructure
  • amidation
  • amines
  • heterogeneous catalysis
  • levulinic acid
  • molecular hydrogen
  • pyrrolidinones
  • reductive amination
  • renewables
  • single-atom catalysts
  • sustainable synthesis

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