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Synfacts 2023; 19(07): 0657
DOI: 10.1055/s-0042-1751918
DOI: 10.1055/s-0042-1751918
Synthesis of Materials and Unnatural Products
Pyrenylenes of Varied Size from One Pot
Popp D,
Elbert SM,
Barwig C,
Petry J,
Rominger F,
Mastalerz M.
*
Ruprecht-Karls-Universität Heidelberg, Germany
Palladium-Catalyzed Cyclization of a Pyryne Precursor to Higher Pyrenylenes.
Angew. Chem. Int. Ed. 2023;
62: e202219277
DOI: 10.1002/anie.202219277
Palladium-Catalyzed Cyclization of a Pyryne Precursor to Higher Pyrenylenes.
Angew. Chem. Int. Ed. 2023;
62: e202219277
DOI: 10.1002/anie.202219277
Key words
Palladium-catalyzed oligocyclization - pyrenylenes - Kobayashi-type aryne - pentaphenylene
Significance
When a palladium-catalyzed cyclization procedure is applied to the Kobayashi-type aryne precursor of a pyrene derivative, a set of cyclic oligomers of pyrenylenes of varied sizes, consisting of two up to five pyrene units, are isolated. A plausible Pd-mediated, step-wise cyclo-oliogomerization mechanism is suggested on the basis of DFT calculations.
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Comment
One of the most fascinating results presented by the work is revealing the structures of some large oligophenylenes in the crystalline state, including (cyclo)pentaphenylene, which are embedded as the core of various pyrenylenes.
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Publication History
Article published online:
16 June 2023
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