Lithium phosphonate umpolung catalysts: Do fluoro substituents increase the catalytic activity?
2011

Fluoro Substituents and Catalytic Activity in Lithium Phosphonate Umpolung Catalysts

publication Evidence: moderate

Author Information

Author(s): Gliga Anca, Goldfuss Bernd, Neudörfl Jörg M, Rueping Magnus

Primary Institution: Department für Chemie, Universität zu Köln

Hypothesis

Do fluoro substituents increase the catalytic activity?

Conclusion

Fluorinated phosphonates showed decreased catalytic activity compared to nonfluorinated ones in benzoin couplings.

Supporting Evidence

  • Fluorinated phosphonates were synthesized and tested in benzoin coupling reactions.
  • Yields ranged from 5% to 44% for the different phosphonates used.
  • The study found that the expected increase in catalytic activity with fluorinated phosphonates was not realized.

Takeaway

The study looked at how adding fluorine to certain chemicals affects their ability to help make other chemicals. It found that adding fluorine actually made them less effective.

Methodology

Different fluorinated and nonfluorinated phosphonates were synthesized and tested as precatalysts in benzoin coupling reactions.

Limitations

The study did not confirm the expected increase in catalytic activity with fluorinated phosphonates.

Digital Object Identifier (DOI)

10.3762/bjoc.7.138

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