Boron-mediated sequential alkyne insertion and C–C coupling reactions affording extended π-conjugated molecules
| Autor: | Haruka Sugiyama, Sho Muranaka, Fatin Hajjaj, Kumiko Takenouchi, Yoshiaki Shoji, Naoki Tanaka, Naoki Shigeno, Takanori Fukushima |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Chrysene
chemistry.chemical_classification Multidisciplinary 010405 organic chemistry Science General Physics and Astronomy Alkyne General Chemistry Phenanthrene Conjugated system 010402 general chemistry 01 natural sciences Combinatorial chemistry General Biochemistry Genetics and Molecular Biology Coupling reaction Article 0104 chemical sciences Metal chemistry.chemical_compound chemistry visual_art visual_art.visual_art_medium Molecule Moiety |
| Zdroj: | Nature Communications, Vol 7, Iss 1, Pp 1-7 (2016) Nature Communications |
| ISSN: | 2041-1723 |
| Popis: | 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/Csp2–Csp2 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 π-conjugated systems. Coupling reactions to form C–C bonds typically require transition metals. Here the authors report that an organoboron compound can allow sequential alkyne insertion and unusual oxidative deborylation/Csp2 –Csp2 coupling, enabling the transformation of acetylenes into extended π-conjugated molecules. |
| Databáze: | OpenAIRE |
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