Convenient Synthesis of Dibenzo[<i>a</i>,<i>h</i>]anthracenes and Picenes via C–H Arylation of Acetophenones with Arenediboronates

Kitazawa, Kentaroh; Kochi, Takuya; Nitani, Masashi; Ie, Yutaka; Aso, Yoshio; Kakiuchi, Fumitoshi

doi:10.1246/cl.2011.300

Cited by 38 publications

(17 citation statements)

References 55 publications

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“…The Ru-catalyzed carbonyl-directed C-H/C-B coupling has also been applied to synthesize picene and dibenzoanthracenes as candidates for organic field effect transistor (OFET) materials as well as for the synthesis of hexaarylanthracenes. [43]…”

Section: Perylene Bisimidesmentioning

confidence: 99%

Synthesis of Extended π‐Systems through C–H Activation

2014

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Activation of aromatic CH bonds by a transition metal catalyst has received significant attention in the synthetic chemistry community. In recent years, rapid and site-selective extension of π-electron systems by C-H activation has emerged as an ideal methodology for preparing organic materials with extended π-systems. This Review focuses on recently reported π-extending C-H activation reactions directed toward new optoelectronic conjugated materials.

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Section: Perylene Bisimidesmentioning

confidence: 99%

Synthesis of Extended π‐Systems through C–H Activation

2014

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“…In the second step, the conversion of the acetyl group of compounds 118 to an ethynyl group afforded diethynylterphenyls 119 . In the last step, a platinum-catalyzed intramolecular cycloaromatization of 119 provided dibenzo[ a , h ]anthracenes 120 bearing methyl and alkoxy groups in low to moderate yields (26–51%) [ 61 ].…”

Section: Reviewmentioning

confidence: 99%

Recent advances in the syntheses of anthracene derivatives

Baviera

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2021

Beilstein J. Org. Chem.

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Anthracene and anthracene derivatives have been extensively studied over the years because of their interesting photophysical, photochemical, and biological properties. They are currently the subject of research in several areas, which investigate their use in the biological field and their application in OLEDs, OFETs, polymeric materials, solar cells, and many other organic materials. Their synthesis remains challenging, but some important preparative methods have been reported, especially in the last decade. This review presents an update of the recent strategies that have been employed to prepare anthracene derivatives. It encompasses papers published over the last twelve years (2008–2020) and focuses on direct and indirect methods to construct anthracene and anthraquinone frameworks.

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“…Unter diesen Bedingungen wurde ein PBI 47 in guten Ausbeuten in mehrere tetraarylierte PBIs 48 a – f umgewandelt (Schema ). Die Ru‐katalysierte durch Carbonylgruppen gesteuerte C‐H/C‐B‐Kupplung wurde auch zur Synthese von Picen und Dibenzoanthracenen als Kandidaten für organische Feldeffekttransistoren (OFETs) sowie zur Synthese von Hexaarylanthracenen eingesetzt 43…”

Section: Erweiterung Von π‐Systemen Durch Bildung Intermolekularerunclassified

Synthese von Materialien mit erweitertem π‐System durch C‐H‐Aktivierung

2014

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Die Aktivierung von aromatischen C‐H‐Bindungen durch einen Übergangsmetallkatalysator ist ein wichtiges Thema in der Synthesechemie. In den letzten Jahren hat sich die schnelle und regiospezifische Erweiterung von π‐Systemen durch C‐H‐Aktivierung zu einer idealen Methode zur Herstellung von organischen Materialien mit ausgedehntem π‐System entwickelt. Dieser Aufsatz fasst neuere Reaktionen zur C‐H‐Aktivierung für die Erweiterung von π‐Systemen im Hinblick auf neue optoelektronische konjugierte Materialien zusammen.

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Convenient Synthesis of Dibenzo[a,h]anthracenes and Picenes via C–H Arylation of Acetophenones with Arenediboronates

Cited by 38 publications

References 55 publications

Synthesis of Extended π‐Systems through C–H Activation

Synthesis of Extended π‐Systems through C–H Activation

Recent advances in the syntheses of anthracene derivatives

Synthese von Materialien mit erweitertem π‐System durch C‐H‐Aktivierung

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