Domino Cross-Scholl Reaction of Tetracene with Molecular Benzene: Synthesis, Structure, and Mechanism

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...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 20; pp. 7921 - 7926
Main Authors Mishima, Daisuke, Nakanishi, Haruka, Tsuboi, Yui, Kishimoto, Yusho, Yamanaka, Yohei, Harada, Ai, Togo, Masahiro, Yamada, Yuto, Muraoka, Masahiro, Murata, Michihisa
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.10.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AROMATIC-COMPOUNDS
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Summary: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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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02921