Radical Bicyclization of <i>N</i> -Phenyl-4-pentenamides: A Modular and Selective Synthesis of γ-Lactam-Substituted Chroman-4-one and Indanone Hybrid Molecules

Herein, we report a modular and efficient silver-catalyzed domino radical bicyclization of <i>N</i>-phenyl-4-pentenamides with 2-(allyloxy)benzaldehydes and 2-allylbenzaldehydes, enabling the selective synthesis of γ-lactam-containing chroman-4-one and indanone hybrids in moderate to good yields. This transformation proceeds under mild conditions and features high step- and atom-economy, constructing two C-C bonds and one C-N bond in a single step within 30 min. Notably, it affords five-membered carbocycles or six-membered oxygen heterocycles with excellent regioselectivity.