Palladium-catalyzed cyclization of a pyryne precursor to higher pyrenylenes
The palladium catalyzed cyclotrimerization of ortho-silylaryl triflates as aryne precursors is meanwhile an established method to synthesize polycyclic aromatic hydrocarbons (PAHs) with triphenylene cores. During the palladium-catalyzed reaction of a pyrene with an o-silylaryl triflate moiety in the...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
May 2, 2023
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| In: |
Angewandte Chemie
Year: 2023, Volume: 135, Issue: 19 |
| ISSN: | 1521-3757 |
| DOI: | 10.1002/ange.202219277 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/ange.202219277 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ange.202219277 
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| Author Notes: | Dennis Popp, Sven M. Elbert, Chantal Barwig, Julian Petry, Frank Rominger, Michael Mastalerz |
| Summary: | The palladium catalyzed cyclotrimerization of ortho-silylaryl triflates as aryne precursors is meanwhile an established method to synthesize polycyclic aromatic hydrocarbons (PAHs) with triphenylene cores. During the palladium-catalyzed reaction of a pyrene with an o-silylaryl triflate moiety in the K-region higher homologues with central eight- and ten-membered rings (the pyrenylenes) were found, besides the expected trimer and a protocol was developed to isolate all members of this series. This unprecedented new class of PAHs was fully investigated by all means, including X-ray diffraction of single-crystals, UV/Vis and fluorescence spectroscopy and theoretical calculations. Supported by density-functional theory (DFT) calculations, a mechanism of all higher cyclooligomers is proposed. |
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| Item Description: | Gesehen am 04.09.2023 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3757 |
| DOI: | 10.1002/ange.202219277 |