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Synthesis of 1,2-borazaronaphthalenes from imines by base-promoted borylation of C-H bond
- Source :
- The Journal of organic chemistry. 80(8)
- Publication Year :
- 2015
-
Abstract
- A new route from benzylic imines permits the synthesis of 1,2-borazaronaphthalenes in good yields. The reaction involves formation of the enamidyl dibromoborane, which undergoes base-promoted borylation of the nearby aromatic C–H bond. Electrophilic attack of the boron species onto the benzylic arene is supported by the slow borylation of arenes substituted with electron-withdrawing groups. The resultant boron bromides can be easily substituted with lithium reagents to provide a range of products. The electronic properties of these 1,2-borazaronaphthalene derivatives have been investigated by UV–vis and fluorescence spectroscopy.
Details
- ISSN :
- 15206904
- Volume :
- 80
- Issue :
- 8
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....14b154d356f9dd03cf0f7b0972202a7a