Facile Aromatic Finkelstein Iodination (AFI) Reaction in 1,3-Dimethyl-2-imidazolidinone (DMI)

Abstract

In this communication, we report the superior role of 1,3-dimethyl-2-imidazolidinone (DMI) as a solvent for aromatic Finkelstein iodination (AFI), the conversion of aryl bromides to aryl iodides. DMI accelerates the reaction rate and affords product(s) that could not be prepared using previous methods. Our findings for AFI avoid the use of toxic solvents such as N,N-dimethylformamide and hexamethylphosphoramide.

GRAPHICAL ABSTRACT

Keywords:

• Aromatic Finkelstein reaction
• aromatic nucleophilic substitution reaction
• DMI
• iodination

ACKNOWLEDGMENTS

This work was supported in part by Grants-in-Aid for Scientific Research (Category B: 08091971 and Priority Areas: 08071557 to K.-I. S.) from the Ministry of Education, Culture, Sports, Science, and Technology. We appreciate the technical assistance provided by Yumiko Iwaki, Tokyo Metropolitan University.