Abstract Photo‐induced radical silylation cyclization of N ‐propargylindoles/(3‐phenoxyprop‐1‐yn‐1‐yl)benzenes with silylboronates or tris(trimethylsilyl)silane was finished, which gave diverse silylated fused cycles. This cascade system featured simple/mild conditions, and good substrate scopes/yields. Meanwhile, a range of scaled‐up experiments, preparation of one silylated active molecule, and mechanistic exploration were performed to examine the application and reaction process.