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Article

Ullmann-type C−Se Cross-Coupling in the Hydantoin Family:Synthesis, Mechanistic Studies, and Tests of Biological Activity

Journal of Organic Chemistry. 2020. Vol. 85. No. 5. P. 3160-3173.
Vyhivskyi O., Laikov D., Finko A., Скворцов Д. А., Zhirkina I., Tafeenko V., Zyk N., Majouga A., Beloglazkina E.

An attractive strategy for C−Se bond formation by Ullmann-type copper(I)-promoted cross-coupling is developed. A wide range of aryliodides reacts with various disubstituted 2- selenohydantoins under mild conditions and provides Se-arylated imidazolines in moderate to high yields. Computational mechanistic studies show the oxidative addition/intramolecular reductive elimination likely to be the lowest-energy pathway. Cytotoxic activity of all 43 reaction products has been tested in vitro against MCF7 and A549 cancer cell lines with VA13 and MCF10a control cells.