Ring-opening iodination and bromination of unstrained cycloalkanols through β-scission of alkoxy radicals

Abstract

Ring-opening iodination or bromination of unstrained cycloalkanols with NaI or NaBr and PhI(OAc)₂ under visible light irradiation is developed. In this protocol the concentration of I₂ is modulated through the generation of triiodide (I₃^-), thus significantly avoiding undesired side reactions. The reaction is under mild conditions and has a wide substrate scope, thus providing a practically useful method for accessing ω-iodo or ω-bromoketones.