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Tetrahedron. 2011 Sep 30;67(39):7461-7469.

Regioselective Iodination of Chlorinated Aromatic Compounds Using Silver Salts.

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The University of Iowa, Department of Occupational and Environmental Health, University of Iowa Research Park, 124 IREH, Iowa City, IA 52242, USA.


The iodination of chlorinated aromatic compounds using Ag(2)SO(4)/I(2), AgSbF(6)/I(2), AgBF(4)/I(2) and AgPF(6)/I(2) offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para and para iodinated product, respectively. In the case of chlorobenzene and 3-chlorotoluene, AgSbF(6)/I(2), AgBF(4)/I(2) and AgPF(6)/I(2), but not Ag(2)SO(4)/I(2), selectively introduced the iodine in para position to the chlorine substituent.

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