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Small Molecule Activation on a Base-stabilized Phosphinidene.

Aliona G Baradzenka1, Melanie Pilkington1, Anton Dmitrienko1

  • 1Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, Ontario, L2S 3A1, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 27, 2023
PubMed
Summary

The reduction of phosphinoamidinate dichloride yields a phosphinidene. This reactive intermediate undergoes diverse reactions, including adduct formation, metathesis, oxidation, and phospha-Wittig reactions, showcasing its versatile chemistry.

Keywords:
boranesphosphinesphosphinidenessilanessmall molecule activation

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Area of Science:

  • Inorganic Chemistry
  • Organophosphorus Chemistry
  • Reactive Intermediates

Background:

  • Phosphinidenes are highly reactive species with a divalent phosphorus atom.
  • Stabilization of phosphinidenes is crucial for studying their reactivity.
  • Phosphinoamidinate ligands offer a unique scaffold for stabilizing reactive phosphorus centers.

Purpose of the Study:

  • To synthesize and characterize a novel phosphinoamidinate-supported phosphinidene.
  • To investigate the reactivity of this phosphinidene with various small molecules and reagents.
  • To explore new synthetic pathways and understand the reaction mechanisms involving phosphinidenes.

Main Methods:

  • Reduction of a phosphinoamidinate dichloride precursor using KC8 to generate the phosphinidene.
  • Reactions of the phosphinidene with N-heterocyclic carbenes, boranes, silanes, phosphines, tetrachlorobenzoquinone, benzaldehyde, and phenylisocyanate.
  • Spectroscopic characterization (NMR, X-ray crystallography) of the resulting products.

Main Results:

  • Successful synthesis of the phosphinoamidinate-supported phosphinidene (NP)P.
  • Formation of an NHC-adduct featuring an iminophosphinyl group.
  • Metathesis reactions yielding (NP)Bpin, (NP)SiH2Ph, and a base-stabilized phosphido-phosphinidene.
  • Oxidation of P(I) to P(III) and ligand oxidation to P(V) with tetrachlorobenzoquinone.
  • Phospha-Wittig reaction with benzaldehyde and addition reaction with phenylisocyanate.

Conclusions:

  • The phosphinoamidinate ligand effectively stabilizes the reactive phosphinidene intermediate.
  • The phosphinidene exhibits diverse reactivity, participating in addition, metathesis, and redox reactions.
  • This study expands the known chemistry of phosphinidenes and provides insights into their synthetic utility.