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DOI: 10.1055/s-2003-41405
Acid-Mediated Halogen Exchange in Heterocyclic Arenes: A Highly Effective Iodination Method
Publikationsverlauf
Publikationsdatum:
28. August 2003 (online)
Abstract
Heterocyclic arenes including pyridyl, quinolyl, and isoquinolyl chlorides have been converted to their corresponding iodides in good to high yields via acid-mediated nucleophilic halogen exchange with sodium iodide. This procedure avoids the use of transition metals, harsh reaction conditions, and affords highly regioselective halide exchange. Chloride substituents in position 2 and 4 of pyridines and quinolines are readily substituted by iodide in 75-91% and conversion of 1-chloroisoquinoline to its iodide derivative was found to proceed with 90% yield. Positions that are not activated for nucleophilic aromatic substitution proved to be inert to halide exchange. Regioselective chloride/iodide exchange in 4,7-dichloroquinoline hydrochloride gave 7-chloro-4-iodoquinoline, an important precursor of anti-malaria drugs, in almost 90% yield.
Key words
chloride/iodide exchange - aryl iodides - nucleophilic aromatic substitution - cross-coupling reactions.
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References
Only starting material was recovered after treatment of 3-chloropyridine hydrochloride with NaI.
st-12Small amounts of starting materials were recovered in both cases.
st-13All known compounds show 1H NMR and 13C NMR spectroscopy and mass spectrometry data consistent with the given structures.