19261-04-2Relevant academic research and scientific papers
Catalyst-Free Synthesis of O-Heteroacenes by Ladderization of Fluorinated Oligophenylenes
Feofanov, Mikhail,Akhmetov, Vladimir,Takayama, Ryo,Amsharov, Konstantin
, p. 5199 - 5203 (2021/02/21)
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.
