Please use this identifier to cite or link to this item: http://dx.doi.org/10.25673/76938
Title: Catalyst-free synthesis of O-heteroacenes by ladderization of fluorinated oligophenylenes
Author(s): Feofanov, Mikhail
Akhmetov, Vladimir
Takayama, Ryo
Amsharov, Konstantin
Issue Date: 2021
Type: Article
Language: English
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.
URI: https://opendata.uni-halle.de//handle/1981185920/78892
http://dx.doi.org/10.25673/76938
Open Access: Open access publication
License: (CC BY-NC-ND 4.0) Creative Commons Attribution NonCommercial NoDerivatives 4.0(CC BY-NC-ND 4.0) Creative Commons Attribution NonCommercial NoDerivatives 4.0
Sponsor/Funder: Publikationsfonds MLU
Journal Title: Angewandte Chemie
Publisher: Wiley-VCH
Publisher Place: Weinheim
Volume: 60
Issue: 10
Original Publication: 10.1002/anie.202007427
Page Start: 5199
Page End: 5203
Appears in Collections:Open Access Publikationen der MLU