Premium
Catalyst‐Free Synthesis of O‐Heteroacenes by Ladderization of Fluorinated Oligophenylenes
Author(s) -
Feofanov Mikhail,
Akhmetov Vladimir,
Takayama Ryo,
Amsharov Konstantin
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007427
Subject(s) - synthon , chemistry , catalysis , annulation , oxygen , combinatorial chemistry , nucleophile , nucleophilic substitution , nucleophilic addition , radical , organic chemistry
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 O 2− 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.