AI Article Synopsis
- Treatment of 2-phenylpyridines with a 9-BBN dimer and iron salt catalyst leads to the formation of ortho-borylated products, achieving moderate to excellent yields.
- The reaction can be scaled to gram quantities and is effective on heteroaromatic compounds, demonstrating good functional group compatibility.
- This C-H borylation method is significantly cheaper than previous palladium-catalyzed approaches, and the resulting products show unique fluorescence properties due to their intramolecular B-N interactions and electron push-pull structures.
Article Abstract
Treatment of 2-phenylpyridines (or their analogs) with a 9-bicycloboranonane dimer (9-BBN dimer) in the presence of a catalytic amount of a commercially available iron salt, FeBr, gave ortho-borylated products in moderate to excellent yields with good functional group tolerance. The reaction proceeded in good yield, even in gram-scale, and also occurred at the C-H bond of heteroaromatic compounds. The cost of the C-H borylation is dramatically lower than that of a previously reported similar palladium-catalyzed reaction. The products exhibit an intramolecular B-N Lewis acid-base interaction and fluoresce in both solution and solid states due to their electron push-pull structures.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b01423 | DOI Listing |
Publication Analysis
Top Keywords
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!