Organic Chemistry Portal



Direct α-Iodination of Aryl Alkyl Ketones by Elemental Iodine Activated by Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)

Marjan Jereb, Stojan Stavber*, Marko Zupan

*Laboratory for Organic and Bioorganic Chemistry, ‘Jozef Stefan' Institute and Department of Chemistry, University of Ljubljana, Jamova 39, 1000 Ljubljana, Email:

M. Jereb, S. Stavber, M. Zupan, Synthesis, 2003, 853-858.

DOI: 10.1055/s-2003-38689


Selective introduction of an iodine atom at the α-carbonyl position in various aryl alkyl ketones was effectively achieved by reaction of target molecules with elemental iodine in the presence of N-F reagents such as F-TEDA-BF4 (Selectfluor) as iodination mediators and methanol as the solvent.

see article for more examples

Key Words

iodine, ketones, regioselectivity, fluorine, α-iodination, selectfluor

ID: J66-Y2003-1820