Abstract:
Incorporation of the trifluoromethyl group in biologically active compounds have
always been regarded of high importance in medicinal and pharmaceuticals chemistry.
The selective installation of the trifluoromethyl group onto small molecules can enhance
many of its physicochemical and pharmacokinetic properties. The electron-withdrawing
CF3 moiety on pharmaceuticals provide metabolic and thermal stability, increases
electrostatic interaction with a target molecule in the body, improves cellular membrane
permeability and lipophilicity and have many other usage and advantages in biology and
agrochemicals. As the field of photoredox catalysis develops, the need to find new
methodologies to help in modern drug discovery becomes crucial as well. Herewith we
have reported a detailed novel study for the incorporation of trifluoromethyl group in
heteroarenes using cadmium selenide (CdSe), a commercially available semiconductor
photocatalyst. The new catalyst is air and moisture stable, can tolerate high reactive
radical intermediates and can be readily recovered by simple centrifugation after use
and can be reused several times. Along with a wide variety of substrate scope, we have
shown the applicability of our developed methodology to medicinal chemistry and drug
development through examples of trifluoromethylation of some biologically active
compounds such as RNA-base Uracil, plant hormone Heteroauxin and flavorant
Vanillin.
