Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C−F Bond Activation on Aluminum Oxide

Akhmetov V, Feofanov M, Troyanov S, Amsharov K (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Chemistry - A European Journal Wiley

DOI: 10.1002/chem.201901450

Abstract

The unique nature of the alumina-mediated cyclodehydrofluorination gives the opportunity to execute the preprogrammed algorithm of the C−C couplings rationally built into a precursor. Such multi-assemblies facilitate the construction of the carbon-skeleton, superseding the conventional step-by-step by the one-pot intramolecular assembly. In this work, the feasibility of the alumina-mediated C−F bond activation approach for multi-assembly is demonstrated on the example of a fundamental bowl-shaped polycyclic aromatic hydrocarbon (diindenochrysene) through the formation of all “missing” C−C bonds at the last step. Beside valuable insights into the reaction mechanism and the design of the precursors, a facile pathway enabling the two-step synthesis of diindenochrysene was elaborated, in which five C−C bonds form in a single synthetic step. It is shown that the relative positions of fluorine atoms play a crucial role in the outcome of the assembly and that governing the substituent positions enables the design of effective precursor molecules “programmed” for the consecutive C−C bond formations. In general, these findings push the state of the field towards the facile synthesis of sophisticated bowl-shaped carbon-based nanostructures through multi-assembly of fluoroarenes.

Authors with CRIS profile

Vladimir Akhmetov Lehrstuhl für Organische Chemie II Mikhail Feofanov Lehrstuhl für Organische Chemie II Konstantin Amsharov Lehrstuhl für Organische Chemie II

Involved external institutions

Humboldt-Universität zu Berlin DE Germany (DE)

How to cite

APA:

Akhmetov, V., Feofanov, M., Troyanov, S., & Amsharov, K. (2019). Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C−F Bond Activation on Aluminum Oxide. Chemistry - A European Journal. https://dx.doi.org/10.1002/chem.201901450

MLA:

Akhmetov, Vladimir, et al. "Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C−F Bond Activation on Aluminum Oxide." Chemistry - A European Journal (2019).

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