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Aryl-aryl coupling in a polycyclic aromatic hydrocarbon with embedded tetracoordinate boron centre
Sven Kirschner1, Song-Song Bao2, Melina K Fengel1
1Institut für Anorganische Chemie, Goethe-Universität Frankfurt, Max-von-Laue Strasse 7, 60438 Frankfurt am Main, Germany. Matthias.Wagner@chemie.uni-frankfurt.de.
Organic & Biomolecular Chemistry
|May 9, 2019
Summary
Researchers synthesized a novel oxaboraphenanthrene by reacting a diboraanthracene with MesLi. This reaction involves B-Mes addition, C-C bond formation, and subsequent oxygen insertion, yielding a yellow compound.
Area of Science:
- Organoboron chemistry
- Synthetic organic chemistry
- Materials science
Background:
- 9,10-dihydro-9,10-diboraanthracene (DBA) derivatives are explored for unique electronic properties.
- Organoboron compounds offer versatile reactivity for constructing complex molecular architectures.
Purpose of the Study:
- To synthesize and characterize a novel biphenylene-containing oxaboraphenanthrene.
- To investigate the reaction mechanism of MesLi addition to DBA and subsequent transformations.
Main Methods:
- Reaction of biphenylene-containing 9,10-dihydro-9,10-diboraanthracene (DBA) with 2 equivalents of MesLi.
- Column chromatography for product isolation.
- Spectroscopic characterization (UV-Vis absorption).
Main Results:
- Formation of the oxaboraphenanthrene 3 from DBA 2 and MesLi.
- Identification of an intermediate biphenylene-containing borafluorene 4.
- Observation of C-C bond formation and Lewis acid-mediated reactions.
- The product 3 exhibits absorption at λmax = 450 nm and lacks photoluminescence.
Conclusions:
- A new synthetic route to biphenylene-containing oxaboraphenanthrenes has been established.
- The reaction proceeds via anionic intermediates and C-C bond formation.
- The resulting oxaboraphenanthrene possesses distinct photophysical properties.
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