An Acylation-Finkelstein Approach to Radioiodination of Bioactives: The Role of Amide Group Anchimeric Assistance
AuthorFjellaksel, Richard; Dugalic, Damir; Demissie, Taye Beyene; Riss, Patrick; Hjelstuen, Ole Kristian; Sundset, Rune; Hansen, Jørn H
Herein, we report a straightforward sequential acylation‐Finkelstein approach to achieve iodination of amine containing bioactives. The utility was demonstrated by successful radiolabelling with 123I in high radiochemical yield. Moreover, microwave‐assisted Finkelstein reaction can be employed to enhance conversion and reaction rates to obtain the desired iodides. The method is of interest for radioiodination of amine‐containing bioactives. The mechanistic details of the iodination process were studied by kinetics and density functional theory calculations, which revealed the mechanistic complexity of the reaction involving amide group anchimeric assistance. We disclose a number of fundamental aspects of amide group anchimeric assistance in substitution reactions.
This is the peer reviewed version of the following article: Fjellaksel, R., Dugalic, D., Demissie, T.B., Riss, P., Hjelstuen, O.-K., Sundset, R. & Hansen, J.H. (2018). An Acylation-Finkelstein Approach to Radioiodination of Bioactives: The Role of Amide Group Anchimeric Assistance. Journal of Physical Organic Chemistry. https://doi.org/10.1002/poc.3835, which has been published in final form at https://doi.org/10.1002/poc.3835. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.