Cooperative Rh(II) and Pd(0) dual relay catalysis has been developed, which allowed one-pot synthesis of alpha-quaternary allylated indolin-2-ones and benzofuran-2-ones. The catalytic reaction proceeded through the sequential Rh(II)-catalyzed intramolecular aromatic C(sp(2))-H bond functionalization of alpha-diazo carbonyl compounds, followed by Pd(0)-catalyzed allylic alkylation with allylic carbonates to afford the products in high yields (up to 97%).