Related Experiment Video
Updated: Apr 5, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Phosphorus Lewis acids: emerging reactivity and applications in catalysis
1Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6. dstephan@chem.utoronto.ca.
Phosphorus-based Lewis acids are driving innovation in metal-free catalysis. Recent studies highlight their applications in stoichiometric reactivity, Lewis acid catalysis, and frustrated Lewis pair (FLP) chemistry.
Area of Science:
- Main Group Chemistry
- Organophosphorus Chemistry
- Catalysis
Background:
- A resurgence in main group chemistry emphasizes reactivity, leading to new applications.
- Phosphorus compounds, particularly P(iii) and P(v) electrophiles, have historical roles in coordination chemistry.
- Recent research increasingly focuses on the Lewis acidic properties of phosphorus compounds.
Purpose of the Study:
- To review the role of phosphorus-based Lewis acids in recent advances in main group chemistry.
- To highlight applications in stoichiometric reactivity, Lewis acid catalysis, and frustrated Lewis pair (FLP) chemistry.
- To underscore the potential of phosphorus-based Lewis acids in metal-free catalytic processes.
Main Methods:
- Literature review of studies focusing on phosphorus-based Lewis acids.
- Analysis of applications in stoichiometric reactions.
- Examination of catalytic applications and frustrated Lewis pair (FLP) reactivity.
Main Results:
- Phosphorus-based Lewis acids are effective in stoichiometric transformations.
- These compounds show significant utility in Lewis acid catalysis.
- Novel applications in frustrated Lewis pair (FLP) chemistry have been developed.
Conclusions:
- Phosphorus-based Lewis acids are versatile reagents in modern chemistry.
- They represent a powerful platform for developing metal-free catalytic systems.
- Further exploration of P-based Lewis acids promises continued advancements in catalysis.
Related Concept Videos
Lewis Acids and Bases
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
Lewis Acids and Bases
Carboxylic Acids to Acid Chlorides
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...

