An efficient and clean approach for the oxidative amination of indole derivatives with phenothiazines is developed under copper‐catalyzed aerobic conditions. The reaction is carried out via the cross‐coupling of indole radical cation and phenothiazine radical in air. This approach offers a new perspective in the application of phenothiazine as a nitrogen group source for C−N bond formation reactions.
An efficient electrooxidative double C-H/C-H coupling of phenols with 3-phenylbenzothiophene has been developed under external oxidant- and catalyst-free conditions. This strategy could enable the highly tunable access to benzothiophene derivatives...
The electroreduction of nitrobenzene in deoxygenated acid solution generates predominantly either paminophenol or aniline via the common electrochemically generated intermediate, phenylhydroxylamine. Square wave current control increases the reaction selectivity for paminophenol, which is produced in a chemical pathway from the intermediate over that obtained at the average current of the oscillation. Data collected under electrokinetic-controlled reaction conditions on a planar copper electrode in a water-propanol-sulfuric acid medium show an order of magnitude increase in selectivity at 100 Hz over that measured at the average direct current. The electrode is depolarized under periodic current control which results in lower rates of undesired electrochemical reactions with a consequential increase in chemical product selectivity. Implications and limitations of periodic electrochemical reaction rate control are discussed. Changes in the Modulated Electroreduction of Nitrobenzene, M.S. Thesis, North Carolina State Univ. (1984). Fedkiw, P. S., and W. Scott, "Selectivity Changes in Electrochemical Reaction Sequences by Modulated Potential Control," J . Electrochem. Soc., 131,1,304 (1984). Pletcher D., and J. Marquez, "A Study of the Electrochemical Reduction of Nitrobenzene in Acidic Propanol/Water," 1. Appl. Electrochem., 10, 567 (1980).
Copper catalyzed aerobic oxidation enables the tandem selective and efficient transformation of N‐pyridylindole for the construction of 11H‐pyrido[2,1‐b]quinazolin‐11‐ones. The reaction shows good efficiency to accomplish the aerobic oxidation. Mechanistic investigation indicated the facile oxidation of N‐pyridylindole underwent the single‐electron‐transfer oxidation, the capture of molecular oxygen and the extrusion of carbon monoxide to deliver the desired 11H‐pyrido[2,1‐b]quinazolin‐11‐ones.
Several polycyclic aromatic hydrocarbons are delivered at room temperature by copper-catalyzed aerobic oxidative C−H/C−H [4 + 2] annulation of alkyl-substituted 3-arylindole derivatives. Specifically, dual aryl C−H functionalization is furnished under mild conditions through the 1,2-migration of copper catalyst and regioselective alkyne insertion. Mechanistic experiments demonstrate that the C−H bond cleavage on the indole and phenyl rings is not involved in the rate-limiting step.
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