Photoinduced Cascade Synthesis of Oxindoles and Isoquinolinediones

Herein, we developed alkyl radical generation from C(sp³)-H bonds of alkanes via a photoinduced HAT-process without employing an external metal, photocatalyst, and organic peroxide. The generated alkyl radical participates in radical addition and cascade cyclization of <i>N</i>-arylacrylamides/<i>N</i>-acryloyl benzamides to deliver structurally diverse and valuable functionalized oxindoles and isoquinolinediones in moderate to good yields. Preliminary mechanistic studies indicated the generation of aryl radical through homolytic cleavage of Ar-I bonds via direct photoexcitation of aryl iodide.