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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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1
The University of Iowa, Department of Occupational and Environmental Health, University of Iowa Research Park, 124 IREH, Iowa City, IA 52242, USA.

Abstract

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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