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Updated: Aug 15, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Applications of the DIB-BBr3 Protocol in Bromination Reactions
Liangkun Pan1, Ka-Mei Lee1, Yung-Yin Chan1
1Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong Special Administrative Region of the People's Republic of China.
A novel DIB/BBr3 protocol enables diverse bromination reactions, including electrophilic aromatic substitution and C-H functionalization. This method offers a versatile approach for synthesizing various brominated organic compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Non-symmetrical bromoiodanes are valuable reagents in organic synthesis.
- Existing protocols for bromoiodane-mediated reactions are often substrate-specific.
Purpose of the Study:
- To develop and report a versatile DIB/BBr3 protocol for a wide range of bromination reactions.
- To demonstrate the broad applicability of this protocol across different organic transformations.
Main Methods:
- Utilized a DIB/BBr3 system for various bromination reactions.
- Applied the protocol to electrophilic bromination of arenes.
- Investigated carbonyl C-H monobromination, bromolactonization, and bromocarbocyclization.
- Explored intermolecular bromoetherification of olefins and light-triggered C(sp3)-H bromination.
Main Results:
- Successfully achieved electrophilic bromination of arenes.
- Demonstrated efficient carbonyl C-H monobromination.
- Reported successful bromolactonization and bromocarbocyclization reactions.
- Showcased intermolecular bromoetherification of olefins and light-triggered C(sp3)-H bromination.
Conclusions:
- The DIB/BBr3 protocol provides a versatile and effective method for diverse bromination reactions.
- This protocol expands the synthetic utility of bromoiodanes in organic chemistry.
- The reported method offers a valuable tool for accessing various brominated organic molecules.
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