Ionic Liquid Iodinating Reagent for Mild and Efficient Iodination of Aromatic and Heteroaromatic Amines and Terminal Alkynes

Abstract

Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.

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GRAPHICAL ABSTRACT

Keywords:

• Aromatic and heteroaromatic amines
• hexamethylene bis(N-methylimidazolium) bis(dichloroiodate)
• iodination
• ionic liquid
• terminal alkynes

ACKNOWLEDGMENT

We thank the Research Council of the University of Mazandaran for partial support of this work.

Notes

^a Yields refer to isolated products.

^b All products were identified by comparing of melting point and ¹H NMR spectra with those of authentic samples reported in the literature.

^a Reaction conditions: Phenyl acetylene (0.5 mmol), base (0.5 mmol), HMBMIBDCI (0.25 mmol), and solvent (2 ml), rt.

^b Yields refer to isolated product, 1-iodoethynylbenzene.

^a Yields refer to isolated products.

^b All products were identified by comparing ¹H and ¹³C NMR and TLC data with those of authentic samples reported in the literature.

^a Yields refer to isolated products.