Chemistry Student Seminar

Speaker: Salman A. AlSharif, Chemistry Ph.D. Candidate, King Abdullah University of Science and Technology (KAUST)

Abstract

The presence of fluorine atom in organic compounds improves their absorption and disruption in biological systems and the beneficial physiochemical properties of fluorinated compounds have been widely reported. ^{1, 2} In this context, trifluoromethulthiol moiety (SCF₃) is especially important due to its electronwithdrawing property which enhance the stability of molecules in acidic conditions. Moreover, SCF₃-containing compounds can easily cross lipid membrane due to the improved lipophilicity.^{1, 3-5} Recently, electron donor-acceptor (EDA) complex has been employed to develop the photo-induced organic transformations. The complex which consists of an electron-rich species (donor) and electron-deficient species (acceptor) could absorb visible light due to the electronic coupling of their frontier orbitals.⁶ Considering the great advantages of EDA complex and the lack of method to deliver trifluoromethylthiolated alkenes, herein, we report a metal-free light-driven catalytic methodology for the trifluoromethylthiolation of alkene via EDA complex formation. We successfully demonstrated the applicability of this procedure with ten examples of 1,1-diarylethylen with electron-deficient and electron-donating groups as well as six examples of styrene.

References

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6. Crisenza, G. E.;  Mazzarella, D.; Melchiorre, P., Synthetic methods driven by the photoactivity of electron donor–acceptor complexes. Journal of the American Chemical Society 2020, 142 (12), 5461-5476.