Herein, we first describe finely tunable chemoselectivity in arylation of 3-aryl-1,2,4-oxadiazolones with ortho-(trimethylsilyl)phenyl triflates, including O-arylation enabled by catalytic amount of silver nitrate and metal-free N-arylation. Both the arylation reactions can tolerate a series of functional groups, and afford the corresponding products in moderate to good yields.