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Synthesis of Heptagon-Containing Polyarenes by Catalytic C–H Activation

Keigo E. Yamada, Iain A. Stepek, Wataru Matsuoka, Hideto Ito,* Kenichiro Itami*
Angew. Chem. Int. Ed. 2023, in press, e202311770. DOI: 10.1002/anie.202311770.

[Abstract]

Nanocarbons incorporating non-hexagonal aromatic rings – such as five-, seven-, and eight-membered rings – have various intriguing physical properties such as curved structures, unique one- dimensional packing, and promising magnetic, optical, and conductivity properties. Herein, we report an efficient synthetic approach to polycyclic aromatics containing seven-membered rings via a palladium-catalyzed intramolecular Ar–H/Ar–Br coupling. In addition to all-hydrocarbon scaffolds, heteroatom-embedded heptagon-containing polyarenes can be efficiently constructed with this method. Rhodium- and palladium-catalyzed sequential six- and seven-membered ring formations also afford complex heptagon- containing molecular nanocarbons from readily available arylacetylenes and biphenyl boronic acids. Detailed mechanistic analysis by DFT calculations showed the feasibility of seven- membered ring formation by a concerted metalation-deprotonation mechanism. This reaction can serve as a template for the synthesis of a wide range of seven-membered ring-containing molecular nanocarbons.

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