A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)-H functionalization is described,which is promoted by a cooperative action of catalytic CuBr2,2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2.The method provides a practical tool for transformations of alkynes by means of a C-H functionalization strategy,which enables the formation of one C-C bond and multiple C-O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.