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Domino Cross-Scholl Reaction of Tetracene with Molecular Benzene: Synthesis, Structure, and Mechanism
Daisuke Mishima1, Haruka Nakanishi1, Yui Tsuboi2
1Graduate School of Engineering, Osaka Institute of Technology, Osaka 535-8585, Japan.
Abstract:
A domino-type multiple C-H functionalization of tetracene with molecular benzene is reported. Under the typical conditions of the Scholl reaction, a domino reaction occurs between tetracene and six molecules of benzene in one pot to furnish an aromatic compound with a curved π-system. This reaction sequence involves oxidative cross-dehydrogenative coupling/annulation and Friedel-Crafts-type reactions. Eight C-C bonds are formed via this intermolecular domino reaction without mediation by a metal or the assistance of a specific substituent.
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