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A simple solid phase diversity linker strategy using enol phosphonates.

Ian B Campbell1, Jun Guo, Edward Jones

  • 1GlaxoSmithKline, Stevenage, Herts, UK.

Organic & Biomolecular Chemistry
|September 30, 2004
PubMed
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Researchers developed polymer-bound lactam enol phosphonates from simple phenols on polystyrene resin. These compounds can be cleaved using Suzuki coupling to yield 2-arylenamides efficiently.

Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Synthetic Methodology

Background:

  • Lactam enol phosphonates are versatile synthetic intermediates.
  • Developing efficient methods for their preparation and functionalization is crucial.
  • Polymer-supported reagents offer advantages in purification and reaction control.

Purpose of the Study:

  • To develop a novel method for generating polymer-bound lactam enol phosphonates.
  • To investigate the cleavage of these polymer-bound compounds to access valuable 2-arylenamides.
  • To establish a robust and storable synthetic intermediate for further diversification.

Main Methods:

  • Synthesis of polymer-bound lactam enol phosphonates using phenol on polystyrene resin.
  • Application of Suzuki cross-coupling conditions for cleavage.

Related Experiment Videos

  • Purification and characterization of the resulting 2-arylenamides.

    • Main Results:

    • Successfully generated stable and storable polymer-bound lactam enol phosphonates.
    • Demonstrated efficient cleavage using Suzuki cross-coupling.
    • Obtained 2-arylenamides in moderate to good overall yields.

    Conclusions:

    • Polymer-bound lactam enol phosphonates are easily accessible and stable intermediates.
    • Suzuki cross-coupling provides a viable strategy for releasing diverse 2-arylenamides.
    • This method offers a practical approach for synthesizing functionalized amides.