The palladium-catalyzed oxidative C3-alkenylation of anthranils (2,1-benzisoxazoles) with various styrenes has been successfully achieved. The C3-alkenylated anthranils were subsequently utilized in a [4+2]-cycloaddition with in situ generated α,β-unsaturated ketones leading to the synthesis of a diverse range of olefin-containing quinolines. Notably, this reaction exclusively yielded mono-alkenylated products with E-selectivity. The optimized catalytic conditions were compatible with a wide variety of substituted olefins and anthranils, forming various C3-alkenylated anthranils with good yields. To showcase the application of the present methodology, the C3-alkenylated anthranils have been employed as synthons to access a wide range of substituted quinolines.