Palladium-Catalyzed Annulation Reaction of Bay-Diiodinated Arenes with o‑Chloroaromatic Carboxylic Acids to Access Polycyclic Aromatic Compounds

A palladium-catalyzed annulation reaction of bay-diiodinated arenes with o-chloroaromatic carboxylic acids was established. This approach enables the synthesis of a variety of polycyclic aromatic compounds, especially polyalkoxy-substituted polycyclic aromatic compounds, frequently found in discotic...

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Published inJournal of organic chemistry Vol. 89; no. 21; pp. 15665 - 15677
Main Authors Li, Song, Cui, Cheng-Rong, Huang, Na, Wang, Bi-Qin, Feng, Chun, Shi, Yingbo, Xiang, Shi-Kai
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2024
Amer Chemical Soc
Subjects
ambient temperature
aromatic hydrocarbons
Chemistry
Chemistry, Organic
organic chemistry
Physical Sciences
Science & Technology
TRIPHENYLENES
ACTIVATION
2-IODOBIPHENYLS
LIQUID-CRYSTALS
CYCLES
C-C
COPOLYMERS
EXTENSION
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.4c01785

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Summary:A palladium-catalyzed annulation reaction of bay-diiodinated arenes with o-chloroaromatic carboxylic acids was established. This approach enables the synthesis of a variety of polycyclic aromatic compounds, especially polyalkoxy-substituted polycyclic aromatic compounds, frequently found in discotic liquid-crystalline materials. The investigations indicate that the product 2,3,8,9,12,13-hexakis­(hexyloxy)-5-azadibenzo­[fg,op]­tetracene demonstrates favorable room-temperature liquid-crystalline properties.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01785