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.

Department of Advanced Materials and Organic Synthesis Institute of Chemical Process Fundamentals of the Czech Academy of Sciences v v i Rozvojová 135 165 02 Prague 6 Czech Republic

Department of Analytical Chemistry Institute of Chemical Process Fundamentals of the Czech Academy of Sciences v v i Rozvojová 135 165 02 Prague 6 Czech Republic

Department of Inorganic Chemistry Faculty of Science Charles University Prague Hlavova 2030 128 40 Prague 2 Czech Republic

Citace poskytuje Crossref.org

Resolution of 9,10-Diketo[7]helicene and Its Use in One-Step Preparation of Helicene-Based D-A-D Push-Pull Systems