Related Experiment Video
Updated: Mar 25, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Base-Stabilized Phosphinidene Boranes by Silylium-Ion Abstraction
Amy N Price1, Michael J Cowley2
1EaStCHEM, School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK.
Researchers created novel N-heterocyclic carbene (NHC)-stabilized compounds featuring phosphorus-boron (P=B) double bonds. This breakthrough provides new avenues for synthesizing unique chemical structures with potential applications in materials science.
Area of Science:
- Inorganic Chemistry
- Organophosphorus Chemistry
- Organoboron Chemistry
Background:
- Phosphorus-boron compounds are of significant interest due to their unique bonding and reactivity.
- Stabilization of low-coordinate phosphorus species remains a synthetic challenge.
Purpose of the Study:
- To synthesize and characterize novel N-heterocyclic carbene (NHC)-stabilized compounds with P=B double bonds.
- To investigate the reaction mechanism for the formation of these unique species.
Main Methods:
- Reaction of a highly functionalized phosphinoborane (Mes*(SiMe3)P-B(Cl)Cp*) with Lewis bases (DMAP, NHC).
- Characterization of the resulting base-stabilized phosphinidene boranes (Mes*P=B(L)Cp*).
Main Results:
- Successful preparation of NHC-stabilized compounds containing P=B double bonds.
- Demonstration of Me3SiCl elimination as a key step in the formation pathway.
- Identification of transient borylphosphide anions as intermediates generated by Me3Si abstraction.
Conclusions:
- The study reports a new method for accessing base-stabilized phosphinidene boranes.
- The findings expand the scope of known P=B compounds and their synthetic routes.
- This work offers insights into the fundamental reactivity of phosphorus-boron systems.
More Related Videos
Related Concept Videos
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Hydroboration-Oxidation of Alkenes
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Preparation and Reactions of Sulfides

