Scientists from the Zelinsky Institute have developed a unique multicomponent radical reaction

Multiple bonds are one of the key building blocks in modern organic chemistry due to their wide distribution among natural compounds and synthetic intermediates. Reactions that allow several molecules containing these fragments to be combined in one step by forming a new carbon-carbon bond are a promising method for increasing the molecular complexity of the resulting structures.

Within the framework of a joint Russian-German project of the ZIOC scientists under the leadership of Academician V.P. Ananikov the method of intermolecular coupling of thiols, alkynes, and α-vinyl sulfides was developed. The reaction proceeds with high selectivity under the photoredox catalysis conditions without the use of catalysts based on transition metals. It should be especially noted that the key intermediates in the discovered transformation are free radical species known for their low selectivity in chemical transformations. The uniquely high selectivity of the reaction is ensured by the suppression of side processes of hydrogen atom transfer and associative upconversion of the reducing agent. Based on computer simulations, as well as experiments using the modern methods of physicochemical analysis, a probable path for the reaction was proposed.

Source:

Julia. V. Burykina, Andrey D. Kobelev, Nikita S. Shlapakov, Alexander Yu. Kostyukovich, Artem N. Fakhrutdinov, Burkhard König, Valentine P. Ananikov Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction. Angew. Chem. Int. Ed., 61, 2022, e202116888. DOI: 10.1002/anie.202116888.