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Synfacts 2017; 13(07): 0696
DOI: 10.1055/s-0036-1590567
DOI: 10.1055/s-0036-1590567
Synthesis of Materials and Unnatural Products
Chemoselective Aryl–Aryl Coupling through C–F Bond Activation
Papaianina O.
Akhmetov VA.
Goryunkov AA.
Hampel F.
Heinemann FW.
Amsharov KY.
* Lomonosov Moscow State University, Russia and Friedrich Alexander University Erlangen-Nuremberg, Germany
Synthesis of Rationally Halogenated Buckybowls by Chemoselective Aromatic C–F Bond Activation.
Angew. Chem. Int. Ed. 2017;
56: 4834-4838
Synthesis of Rationally Halogenated Buckybowls by Chemoselective Aromatic C–F Bond Activation.
Angew. Chem. Int. Ed. 2017;
56: 4834-4838
Further Information
Publication History
Publication Date:
19 June 2017 (online)
Significance
Bowl-shaped polycyclic aromatic hydrocarbons have emerged as intriguing building blocks for organic electronic materials. The large strain induced by the curved π-system has thus far only been overcome under harsh conditions that are intolerant to functional groups. In this work, the authors demonstrate directed intramolecular aryl–aryl coupling through C–F bond activation.
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Comment
This aryl–aryl coupling method selectively activated C–F bonds in the presence of other halogens, thus allowing further modification after the cyclization. Yields are near quantitative and operationally facile. Several crystal structures have been obtained and properties evaluated through DFT studies.
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