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Domino Dehydrative π‐Extension: A Facile Path to Extended Perylenes and Terrylenes
Author(s) -
Feofanov Mikhail,
Akhmetov Vladimir,
Amsharov Konstantin
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103098
Subject(s) - domino , biphenyl , perylene , phenanthrene , aryl , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , molecule , catalysis , alkyl
Herein, we report a new method for synthesis of extended perylenes and terrylenes. The technique is based on the cascade dehydrative π‐extensions (DPEX) of aryl aldehydes, in which stepwise annulations activate previously “dormant” substituents. Two‐ and fourfold cyclizations of 3‐aryl‐biphenyl‐2,2′‐dicarbaldehydes offer a rapid path to unsymmetrical perylenes and elusive terrylene derivatives, respectively. DPEX of 3,3′′‐(phenanthrene‐1,8‐diyl)bis (([1,1′‐biphenyl]‐2,2′‐dicarbaldehyde)) leads to the biradical structure, which proceeds in situ into oxidative electrocyclization at room temperature. The described domino process complements and expands DPEX approach to a large family of fused acenes and related PAHs.