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Annulative π-Extension of Unactivated Benzene Derivatives through Nondirected C–H Arylation

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Helden,  Gert von
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Citation

Lee, J. B., Jeon, M. H., Seo, J. K., Helden, G. v., Rohde, J.-U., Zhao, B. S., et al. (2019). Annulative π-Extension of Unactivated Benzene Derivatives through Nondirected C–H Arylation. Organic Letters, 21(17), 7004-7008. doi:10.1021/acs.orglett.9b02583.


Cite as: http://hdl.handle.net/21.11116/0000-0004-8519-A
Abstract
Annulative π-extension chemistry provides aconcise synthetic route to polycyclic arenes. Herein, we disclose a nondirected annulation approach of unactivated simple arenes.The palladium-catalyzed 2-fold C−H arylation event facilitates tandem C−C linkage relays to furnish fully benzenoid triphenylene frameworks using cyclic diaryliodonium salts. The inseparable regioisomeric mixture of 1- and 2-methyltriphenylenes is identified by the combined analysis of ion mobility-mass spectrometry, gas-phase infrared spectroscopy, and molecular simulation studies.