Catalyst-Free Synthesis of O-Heteroacenes by Ladderization of Fluorinated Oligophenylenes

Feofanov M, Akhmetov V, Takayama R, Amsharov K (2021)

Publication Type: Journal article

Publication year: 2021

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 60

Pages Range: 5199-5203

Journal Issue: 10

DOI: 10.1002/anie.202007427

Abstract

A novel catalyst-free approach to benzoannulated oxygen-containing heterocycles from fluorinated oligophenylenes is reported. Unlike existing methods, the presented reaction does not require an oxygen-containing precursor and relies on an external oxygen source, potassium tert-butoxide, which serves as an O²⁻ synthon. The radical nature of the reaction facilitates nucleophilic substitution even in the presence of strong electron-donating groups and enables de-tert-butylation required for the complete annulation. Also demonstrated is the applicability of the method to introduce five-, six-, and seven-membered rings containing oxygen, whereas multiple annulations also open up a short synthetic path to ladder-type O-heteroacenes and oligodibenzofurans.

Authors with CRIS profile

Mikhail Feofanov Lehrstuhl für Organische Chemie II Vladimir Akhmetov Lehrstuhl für Organische Chemie II Ryo Takayama Lehrstuhl für Organische Chemie II Konstantin Amsharov Lehrstuhl für Organische Chemie II

How to cite

APA:

Feofanov, M., Akhmetov, V., Takayama, R., & Amsharov, K. (2021). Catalyst-Free Synthesis of O-Heteroacenes by Ladderization of Fluorinated Oligophenylenes. Angewandte Chemie International Edition, 60(10), 5199-5203. https://doi.org/10.1002/anie.202007427

MLA:

Feofanov, Mikhail, et al. "Catalyst-Free Synthesis of O-Heteroacenes by Ladderization of Fluorinated Oligophenylenes." Angewandte Chemie International Edition 60.10 (2021): 5199-5203.

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