Solvent-Selective Alkoxy Radical–Induced Oxidative β-Scission of C–C/C–N Bonds in Spiro Adducts under Blue LED Irradiation

A green and efficient, catalyst-free, solvent-selective, alkoxy radical-induced oxidative β-cleavage of carbon–carbon (C–C)/carbon–nitrogen (C–N) bonds in spiro[pyrrolo[2,1- a ]isoquinoline-1,5′-thiazolidine]-3-carboxylates is reported. The method enables C1/C2 functionalization of the isoquinoline core with a thiazolidine-2,4-dione unit. The reaction proceeds under mild conditions with a broad substrate scope and good functional group tolerance (up to 96% yield), using molecular oxygen and blue LED irradiation (465–470 nm) under additive-free conditions.