Recent Advances in the Application of P(III)-Nucleophiles to Create New P-C Bonds through Michaelis-Arbuzov-Type Rearrangement

Top Curr Chem (Cham). 2024 Mar 8;382(1):10. doi: 10.1007/s41061-024-00456-x.

Abstract

Organophosphorus compounds have long been considered valuable in both organic synthesis and life science. P(III)-nucleophiles, such as phosphites, phosphonites, and diaryl/alkyl phosphines, are particularly noteworthy as phosphorylation reagents for their ability to form new P-C bonds, producing more stable, ecofriendly, and cost-effective organophosphorus compounds. These nucleophiles follow similar phosphorylation routes as in the functionalization of P-H bonds and P-OH bonds. Activation can occur through photocatalytic, electrocatalytic, or thermo-driven reactions, often in coordination with a Michaelis-Arbuzov-trpe rearrangement process, to produce the desired products. As such, this review offers a thorough overview of the phosphorylated transformation and potential mechanisms of P(III)-nucleophiles, specifically focusing on developments since 2010. Notably, this review may provide researchers with valuable insights into designing and synthesizing functionalized organophosphorus compounds from P(III)-nucleophiles, guiding future advancements in both research and practical applications.

Keywords: Michaelis–Arbuzov rearrangement; P(III)-nucleophiles; P−C bond formation.

Publication types

  • Review

MeSH terms

  • Chemistry Techniques, Synthetic
  • Organophosphorus Compounds* / chemistry
  • Phosphines* / chemistry

Substances

  • Organophosphorus Compounds
  • Phosphines