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Issue 20, 2019
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Aryl–aryl coupling in a polycyclic aromatic hydrocarbon with embedded tetracoordinate boron centre

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Abstract

The addition of 2 eq. of MesLi to the biphenylene-containing 9,10-dihydro-9,10-diboraanthracene (DBA) 2 results in the formation of the corresponding oxaboraphenanthrene 3 after column chromatography under ambient conditions. In the initial step, the anionic B–Mes monoadduct of 2 is generated, which eliminates a formal [Mes2B:] ion with concomitant C–C-bond formation (room temperature, 18 h). The resulting biphenylene-containing borafluorene 4 is still sufficiently Lewis acidic to add the second equivalent of MesLi ([4Mes]). Using pristine 9-mesityl-9-borafluorene as a model system, we confirmed that both 4 and [4Mes] should be capable of inserting an oxygen atom to furnish the observed oxaboraphenanthrene scaffold. The biphenylene-containing oxaboraphenanthrene 3 is a yellow compound with an absorption maximum at λmax = 450 nm. Similar to its DBA analogue 2, 3 shows no photoluminescence.

Graphical abstract: Aryl–aryl coupling in a polycyclic aromatic hydrocarbon with embedded tetracoordinate boron centre

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Publication details

The article was received on 15 Mar 2019, accepted on 29 Apr 2019 and first published on 29 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00618D
Org. Biomol. Chem., 2019,17, 5060-5065

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    Aryl–aryl coupling in a polycyclic aromatic hydrocarbon with embedded tetracoordinate boron centre

    S. Kirschner, S. Bao, M. K. Fengel, M. Bolte, H. Lerner and M. Wagner, Org. Biomol. Chem., 2019, 17, 5060
    DOI: 10.1039/C9OB00618D

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