6533b851fe1ef96bd12aa1a0

RESEARCH PRODUCT

Acid-mediated reaction of bis(pyridine)iodonium(I) tetrafluoroborate with aromatic compounds. A selective and general iodination method

Miguel A. García-martínJosé M. GonzálezJosé BarluengaGregorio AsensioGregorio AsensioGregorio AsensioPedro J. Campos

subject

Acid catalysischemistry.chemical_compoundElectrophilic substitutionTetrafluoroboratechemistryOrganic ChemistryPyridineRegioselectivityHalogenationOrganic chemistryBis(pyridine)iodonium(I) tetrafluoroborateChemical society

description

Reaction of aromatic compounds with bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4) in the presence of HBF4 or CF3SO3H in CH2Cl2 at room temperature furnishes monoiodo derivatives with excellent regioselectivity and yields. Use of either acid gives comparable results with activated aromatics, whereas CF3SO3H is much more effective in the iodination of deactivated aromatics. © 1993 American Chemical Society.

https://doi.org/10.1021/jo00060a020