The synthesis of functionalized alanine-based sulphonamides via copper(I)oxide catalyzed N-arylation reaction and the in silico antibacterial studies is reported. The study involved the initial synthesis of substituted p-toluenesulphonamides and substituted benzenesulphonamides by the reaction of alanine with p-toluenesulphonyl chloride and benzenesulphonyl chloride respectively in aqueous basic medium. The synthesized compounds were acetylated by reacting them with acetic anhydride and sodium acetate followed by acylation and amidation to yield amidated p-toluenesulphonamides and benzenesulphonamides respectively. Copper catalyzed N-arylation of the amidated products with aryltriolborates resulted in the synthesis of benzene, and 2-chlorophenyl derivatives of the amidated products. The synthesized compounds were characterized using FTIR, 1HNMR and elemental analysis and the spectra were in agreement with the assigned structures. The insilico antibacterial studies revealed that the compounds possessed significant antibacterial potency and could be further employed as potential anti-bacterial agents when validated with experimental studies. The antimicrobial study revealed that most of the synthesized compounds possess antibacterial activities.