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Regioselective Iodination of Chlorinated Aromatic Compounds Using Silver Salts.

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.

SUBMITTER: Joshi SN

PROVIDER: S-EPMC3170769 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Regioselective Iodination of Chlorinated Aromatic Compounds Using Silver Salts.

Joshi Sudhir N SN Vyas Sandhya M SM Wu Huimin H Duffel Michael W MW Parkin Sean S Lehmler Hans-Joachim HJ

Tetrahedron 20110901 39

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), ...[more]

PMID: 21918585

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