Development, synthesis, computational and in silico investigations of Pd(II)-catalyzed aryl fluorinated and hydroxylated sulfonamides

Abstract

Pd(II)-catalyzed arylfluorination of disubstituted alkenes have been accomplished for the synthesis of synthetically challenging and biologically relevant quaternary fluoro- and hydroxyl sulfonamide substrates. Arylboronic acid was used as cross-coupling partner and a commercially available electrophilic fluorinating source, Selectfluor, acted as a fluoride source. Along with the fluoride product, quaternary hydroxyl product was also observed as side product. A computational study was done on both the hydroxyl and fluoro products in order to study geometrical properties, electronic properties such as ESP surface analysis, frontier molecular orbital (FMO) analysis, and global chemical reactivity descriptors. The nonlinear optical (NLO) properties of both the molecules showed their potential in material sciences. In silico molecular docking studies were performed to study their activity against bacterial strain Staphylococcus aureus TyrRS. Molecular docking studies shows that both the compounds can act as an inhibitor of Staphylococcus aureus TyrRS, however, compound containing fluorine group is slightly more potent as compare to the compound conatining hydroxyl group.