The results of the research conducted at the Zelinsky Institute are placed on the cover of Organic Letters

In the last decade, one of the most rapidly developing fundamental areas of organic chemistry is C–H activation. This approach makes it possible to design complex organic molecules with exceptional selectivity and atom-efficiency. Carrying out C–H activation under photochemical conditions is especially attractive. This method is distinguished by the ability to fine-tune the selectivity of the process, high availability and low loading of photocatalysts, as well as the use of simple and affordable light sources such as LED lamps.

Scientists from the Laboratory for the Study of Homolytic Reactions of the Zelinsky Institute have developed a method for the synthesis of enaminones from vinyl azides and aldehydes by irradiation with visible light. The process is applicable to a wide variety of the starting substrates, including natural ones, and can be successfully implemented under flow conditions. Using modern physicochemical methods of analysis, such as electron paramagnetic resonance spectroscopy and cyclic voltammetry, a probable mechanism for the observed photochemical transformation was proposed. It was shown that the key step of the process is the C–H activation of aldehydes with the formation of acyl radicals.

The results of the study were featured on the cover of the international highly rated journal Organic Letters.

Source:

Stanislav A. Paveliev, Oleg O. Segida, Olga M. Mulina, Igor B. Krylov, Alexander O. Terent’ev Decatungstate-Catalyzed Photochemical Synthesis of Enaminones from Vinyl Azides and Aldehydes // Org. Lett. 2022, 24, 8942–8947. DOI: 10.1021/acs.orglett.2c03364.