150330-35-1Relevant academic research and scientific papers
Sulfonic acid-catalyzed autoxidative carbon-carbon coupling reaction under elevated partial pressure of oxygen
Pinter, Aron,Klussmann, Martin
supporting information; experimental part, p. 701 - 711 (2012/04/23)
An aerobic organocatalytic oxidative C-C bond formation reaction of benzylic C-H bonds with various C-nucleophiles is described. The coupling reaction proceeds by simply stirring the substrates under elevated partial pressure of oxygen in the presence of a sulfonic acid catalyst at room temperature. Elevation of the pressure enables the reaction of a broad scope of nucleophile substrates otherwise showing poor reactivity at ambient pressure. The benzylic C-H bonds of xanthene, acridanes, isochromane and related heterocycles could be functionalized with nucleophiles including ketones, 1,3-dicarbonyl compounds and aldehydes. Electron-rich arenes could be utilized as nucleophiles at elevated temperatures. The reactions are believed to proceed via autoxidation of the benzylic C-H bonds to the hydroperoxides and subsequent nucleophilic substitution catalyzed by sulfonic acids. Copyright
