Planar Tetraindolodipleiadiene via Zirconium-Promoted Intramolecular Indolyl C4–H Homocoupling

Planar Tetraindolodipleiadiene via Zirconium-Promoted Intramolecular Indolyl C4–H Homocoupling

A novel N-rimmed PAH molecule containing a dipleiadiene core (TIDP) was designed and synthesized from indole, wherein a ZrCl4-promoted intramolecular C4–H homocoupling reaction of the indole moieties was the key approach. TIDP exhibited a nearly full planar structure and antiaromaticity of the two e...

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Veröffentlicht in:Organic letters 2022-06, Vol.24 (23), p.4197-4201
Hauptverfasser: Zheng, Xuesong, Huang, Zhenmei, Zheng, Qinze, Wang, Linhua, Zhang, Cheng, Gao, Ge
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel N-rimmed PAH molecule containing a dipleiadiene core (TIDP) was designed and synthesized from indole, wherein a ZrCl4-promoted intramolecular C4–H homocoupling reaction of the indole moieties was the key approach. TIDP exhibited a nearly full planar structure and antiaromaticity of the two embedded heptagonal rings. The extremely stable radical cation TIDP •+·PF6 – was isolated quantitatively by oxidation with AgPF6.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01484