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

• DOI: 10.1021/acs.orglett.9b02583
• Publication Date: 2019-08-12T14:48:05Z
• Authors: Jae Bin Lee; Min Ho Jeon; Jeong Kon Seo; Gert von Helden; Jan-Uwe Rohde; Bum Suk Zhao; Jongcheol Seo; Sung You Hong
• Keywords: 01 natural sciences; 0104 chemical sciences

Annulative π-extension chemistry provides a concise 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.