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Related Experiment Videos

NiCl2-catalyzed hydrophosphinylation.

Patrice Ribière1, Karla Bravo-Altamirano, Monika I Antczak

  • 1Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA.

The Journal of Organic Chemistry
|May 7, 2005
PubMed
Summary
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A novel nickel catalyst efficiently forms phosphorus-carbon bonds by adding alkyl phosphinates to alkynes. This method improves upon previous palladium catalysis, offering high yields for synthesizing organophosphorus compounds.

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Phosphorus-carbon bond formation is crucial in organophosphorus chemistry.
  • Previous methods, like palladium-catalyzed hydrophosphinylation, showed limitations with internal alkynes.

Purpose of the Study:

  • To develop a new catalytic system for efficient phosphorus-carbon bond formation.
  • To improve the addition of alkyl phosphinates to alkynes, especially internal alkynes.

Main Methods:

  • A nickel-based catalytic system using nickel chloride without added ligand.
  • Reaction optimization including microwave heating for accelerated synthesis.

Main Results:

  • High yields achieved in the nickel-catalyzed addition of alkyl phosphinates to various alkynes.

Related Experiment Videos

  • Successful utilization of internal alkynes, which were previously poor substrates.
  • Demonstration of one-pot synthesis for diverse organophosphorus compounds.

    • Conclusions:

    • The developed nickel-based system is highly effective for P-C bond formation.
    • This method provides a versatile route to H-phosphinate esters and related organophosphorus compounds.
    • The protocol offers advantages in yield and substrate scope compared to prior palladium-catalyzed methods.