Aryl–aryl coupling in a polycyclic aromatic hydrocarbon with embedded tetracoordinate boron centre
文献信息
发布日期
2019-04-29
DOI
10.1039/C9OB00618D
影响因子
3.876
作者
Sven Kirschner, Song-Song Bao, Melina K. Fengel, Michael Bolte, Hans-Wolfram Lerner, Matthias Wagner
查看原文
摘要
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.
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来源期刊
Organic & Biomolecular Chemistry
CiteScore:
3.4
自引率:
10.3%
年发文量:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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