期刊
NATURE COMMUNICATIONS
卷 7, 期 -, 页码 -出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms12704
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资金
- KAKENHI from Japan Society for the Promotion of Science (JSPS) [26102008, 26620058]
- JSPS [15J11698]
- Grants-in-Aid for Scientific Research [26102008, 15J11698, 26620058] Funding Source: KAKEN
C-C bond coupling reactions illustrate the wealth of organic transformations, which are usually mediated by organotransition metal complexes. Here, we show that a borafluorene with a B-Cl moiety can mediate sequential alkyne insertion (1,2-carboboration) and deborylation/Csp(2)-Csp(2) coupling reactions, leading to aromatic molecules. The first step, which affords a borepin derivative, proceeds very efficiently between the borafluorene and various alkynes by simply mixing these two components. The second step is triggered by a one-electron oxidation of the borepin derivative, which results in the formation of a phenanthrene framework. When an excess amount of oxidant is used in the second step, the phenanthrene derivatives can be further transformed in situ to afford dibenzo[g,p] chrysene derivatives. The results presented herein will substantially expand the understanding of main group chemistry and provide a powerful synthetic tool for the construction of a wide variety of extended pi-conjugated systems.
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