Photochemical Oxidation Specific to Distorted Aromatic Amines Providing ortho-Diketones

A straightforward visible-light-promoted oxidation of aminohelicenes providing helical ortho-diketones is described. It is shown that the oxidation of amines proceeds via [2 + 2]-cycloaddition reaction with singlet oxygen as an oxidizer and the reaction is specific to distorted aromatic systems. The...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (10), p.3905-3910
Main Authors: Jakubec, Martin, Hansen-Troøyen, Susanne, Císařová, Ivana, Sýkora, Jan, Storch, Jan
Format: Article
Language:English
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Summary:A straightforward visible-light-promoted oxidation of aminohelicenes providing helical ortho-diketones is described. It is shown that the oxidation of amines proceeds via [2 + 2]-cycloaddition reaction with singlet oxygen as an oxidizer and the reaction is specific to distorted aromatic systems. The versatility of the prepared diketones and tetraketones was proven in several heterocycle-forming reactions. The observed adjustment of the physicochemical properties of original molecules is valuable for further development of functional molecules based on helicenes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01190