AI Article Synopsis
- The text discusses a new method for halogenating six-membered heteroarenes like pyridines, quinolines, and isoquinolines, which is important for adding functional groups to these compounds.
- The method uses an electrophilic halogen radical addition technique combined with an -benzyl activation strategy to achieve targeted dihalogenation patterns in pyridines and quinolines, and monohalogenation in isoquinolines.
- The effectiveness and practical use of this halogenation approach were confirmed through larger scale experiments and by applying it to brominate quinoline derivatives with specific biomolecular fragments.
Article Abstract
Regioselective halogenation of six-membered -heteroarenes is crucial for precise functional derivatization. We present a -selective halogenation method for pyridines, quinolines, and isoquinolines via electrophilic halogen radical addition utilizing an -benzyl activation strategy. This method achieves C3- and C5-dihalogenation in pyridines, C3- and C6-dihalogenation in quinolines, and C3-monohalogenation in isoquinolines. The feasibility and potential applications of this method were validated through scale-up reactions and the bromination of quinoline derivatives with biomolecular fragments.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c01643 | DOI Listing |
Publication Analysis
Top Keywords
-benzyl activation
8
activation strategy
8
radical -c-h
4
-c-h halogenation
4
halogenation azines
4
azines -benzyl
4
strategy regioselective
4
regioselective halogenation
4
halogenation six-membered
4
six-membered -heteroarenes
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!