Synthesis of Dibenzothiophene, Dibenzofuran and Carbazole Donor–Acceptor Chromophores

Tue Heesgaard Jepsen; Mogens Larsen; Morten Jørgensen; Mogens Brøndsted Nielsen

doi:10.1055/s-0032-1318484

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(8): 1115-1120
DOI: 10.1055/s-0032-1318484

paper

Synthesis of Dibenzothiophene, Dibenzofuran and Carbazole Donor–Acceptor Chromophores

Tue Heesgaard Jepsen

^aDepartment of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark Fax: +4535320212 eMail: mbn@kiku.dk

^bMedicinal Chemistry Research, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark

,

Mogens Larsen

^bMedicinal Chemistry Research, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark

,

Morten Jørgensen

^bMedicinal Chemistry Research, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark

,

Mogens Brøndsted Nielsen*

^aDepartment of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark Fax: +4535320212 eMail: mbn@kiku.dk

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Abstract

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Abstract

We present efficient synthetic protocols for functionalizing dibenzothiophene, dibenzofuran, and carbazole with hydroxy and nitro or cyano groups. The synthesis of these donor–acceptor chromophores is based on a key Suzuki–Miyaura coupling using an appropriately substituted aromatic boronic acid. Subsequent intramolecular S_NAr reaction allows formation of the dibenzothiophene and dibenzofuran scaffolds, while a carbon–hydrogen activation reaction is employed to afford the carbazole. A final demethylation step unmasks the phenol moiety of the tricyclic chromophores. The UV/Vis absorption properties of the phenol and phenolate forms of these chromophores are also studied.

Key words

dibenzothiophene - dibenzofuran - carbazole - heterocycles - palladium - phenols

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References

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