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Phosphine Organocatalysis.

Hongchao Guo1, Yi Chiao Fan2, Zhanhu Sun1

  • 1Department of Applied Chemistry , China Agricultural University , Beijing 100193 , P. R. China.

Chemical Reviews
|September 28, 2018
PubMed
Summary
This summary is machine-generated.

This review classifies nucleophilic phosphine catalysis based on electrophilic components, primarily those with carbon-carbon multiple bonds like alkenes and alkynes. It organizes reactions by nucleophile type and covers related phosphine-ylide formation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organophosphorus Chemistry

Background:

  • Nucleophilic phosphine catalysis is initiated by phosphine addition to electrophiles, forming zwitterionic intermediates under mild conditions.
  • Understanding the classification of these reactions is crucial for advancing synthetic methodologies.

Purpose of the Study:

  • To systematically review and classify nucleophilic phosphine catalysis reactions.
  • To organize reactions based on the nature of the electrophilic component and the coreactant.

Main Methods:

  • Classification of reactions based on electrophilic starting materials, including those with carbon-carbon multiple bonds (alkenes, allenes, alkynes, MBHADs).
  • Categorization of reactions by the type of coreactant (nucleophiles, dinucleophiles, electrophiles, electrophile-nucleophiles).
  • Inclusion of related reactions such as phosphine-ylide formation and miscellaneous topics.

Main Results:

  • A comprehensive classification of nucleophilic phosphine catalysis is presented, focusing on electrophilic components.
  • Reactions are detailed according to the presence or absence of carbon-carbon multiple bonds in the electrophile.
  • Related catalytic and non-catalytic phosphine-involved transformations are discussed.

Conclusions:

  • This review provides a structured overview of nucleophilic phosphine catalysis, aiding in the understanding and development of new synthetic routes.
  • The classification highlights the versatility of phosphines as catalysts in organic synthesis.