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

Chem Commun (Camb). 2020 May 7;56(37):5002-5005. doi: 10.1039/d0cc01720e. Epub 2020 Apr 2.

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.