Copper-catalyzed click reaction of diclofenac amide analog 42 with acetylene gas provided triazole 88 in 56% yield. Cycloaddition of chlorzoxazone derivative 38 with pentane-2,4-dione resulted in the formation of triazole 89. Additionally, azide 38 can be further converted into phosphorimidate 90 in 92% yield under mild reducing conditions. The bioconjugation of azides (38 and 42) Figure . Further synthetic applications. a For detailed reaction conditions, please refer to the Supporting Information. b Two-step overall yields were indicated. c Diastereomeric ratio (d.r.) was determined by the analysis of 1 H NMR spectra of the crude reaction mixture. with pharmaceuticals and natural product moieties, such as mestranol, mestranol, fenbufen derivatives, via click chemistry provided feasible access to adducts 91-93 in good yields, suggesting the potential applications in the preparation of antibody-drug conjugates and biomolecule labeling. Phenethylamines, including amphetamine and its derivatives, are naturally occurring compounds with promising biological activities for central nervous system treatments, making them appealing in drug development. We then turned our attention to the synthesis of β-phenethylamine drugs from feedstock chemicals (Figure ). The tandem azidation and reduction using commercially available aromatics with propylene enabled the rapid synthesis of norfenfluramine and amphetamine analogs (94-97 and 101). Moreover, this protocol was successfully employed to construct the key synthetic intermediate for bronchial drug protokylol 3c,21 (98) and the adenosine triphosphate (ATP)competitive protein kinase B (Akt) inhibitor CCT128930 (102). 3b