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Updated: Feb 28, 2026
08:46
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
8.3K
Stable Bromiranium Ions with Weakly-Coordinating Counterions as Efficient Electrophilic Brominating Agents
Christoph Ascheberg1, Jonathan Bock1, Florenz Buß2
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstr. 40, 48149, Münster, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 22, 2017
Summary
Sterically demanding bromiranium ions act as potent electrophilic brominating agents. These stable, highly reactive compounds facilitate the halogenation of alkenes and heteroatoms in chemical synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Electrophilic halogenating agents are crucial in chemical synthesis.
- Development of novel, highly reactive, yet stable reagents is an ongoing challenge.
Purpose of the Study:
- To synthesize and characterize sterically demanding bromiranium ions.
- To evaluate their efficacy as electrophilic brominating agents for various substrates.
Main Methods:
- Synthesis of sterically hindered bromiranium ions with weakly coordinating counterions.
- Application of these ions in electrophilic bromination reactions.
- Stability studies under various conditions.
Main Results:
- Demonstrated high reactivity of sterically demanding bromiranium ions as brominating agents.
- Achieved successful electrophilic halogenation of alkenes.
- Enabled halogenation of heteroatoms.
- Observed stability of the reagents, with one stable under ambient conditions.
Conclusions:
- Sterically demanding bromiranium ions represent a new class of highly reactive and stable electrophilic brominating agents.
- These reagents offer a valuable tool for diverse synthetic applications, including alkene and heteroatom halogenation.
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