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Related Experiment Videos

Calcium-mediated intramolecular hydroamination catalysis.

Mark R Crimmin1, Ian J Casely, Michael S Hill

  • 1Department of Chemistry, Imperial College London, Exhibition Road, South Kensington, London, SW7 2AZ, UK.

Journal of the American Chemical Society
|February 17, 2005
PubMed
Summary

Calcium catalysts facilitate intramolecular hydroamination of alkenes and alkynes. This novel approach shows catalytic activity comparable to rare earth metals for aminoalkene and aminoalkyne cyclization.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Intramolecular hydroamination is a key reaction for synthesizing nitrogen-containing heterocycles.
  • Rare earth metal catalysts are commonly used but can be expensive and sensitive.
  • Developing earth-abundant metal catalysts for this transformation is highly desirable.

Purpose of the Study:

  • To report the development of a calcium-based catalyst for intramolecular hydroamination.
  • To investigate the efficacy of a specific beta-diketiminato calcium complex in this reaction.
  • To compare the catalytic performance of the calcium complex with existing rare earth catalysts.

Main Methods:

  • Synthesis and characterization of the beta-diketiminato calcium complex [{HC(C(Me)2N-2,6-iPr2C6H3)2}-Ca{N(SiMe3)2}(THF)].

Related Experiment Videos

  • Catalytic testing of the complex in the intramolecular hydroamination of various aminoalkenes and aminoalkynes.
  • Analysis of reaction products and comparison of catalytic activity.

    • Main Results:

    • The calcium complex effectively catalyzes the intramolecular hydroamination of a range of aminoalkenes and aminoalkynes.
    • The observed catalytic activities are comparable to those of well-established rare earth catalysts.
    • The reaction proceeds via a cyclization mechanism facilitated by the calcium center.

    Conclusions:

    • Calcium complexes, specifically the reported beta-diketiminato derivative, are effective catalysts for intramolecular hydroamination.
    • This finding offers a potentially more economical and accessible alternative to rare earth catalysts for this important synthetic transformation.
    • Further exploration of calcium catalysis in organic synthesis is warranted.