A novel catalytic protocol enables efficient, environmentally benign oxidative coupling of benzofuran-3(2H)-ones with acids and amines. Employing iodide salts as catalysts and ambient air as the sole oxidant, this method delivers straightforward access to 2-acyloxyaminobenzofuran-3(2H)-ones and α-ketoamides with a broad substrate scope, excellent functional group tolerance, and good yields. The approach further demonstrates utility in late-stage functionalization of complex pharmaceuticals, highlighting its synthetic potential.