On the activation of PhICl <sub>2</sub> with pyridine
Tiffany B. Poynder, Analia I. Chamorro Orué, Tania Tania, Lachlan Sharp‐Bucknall, Matthew T. Flynn, David J. D. Wilson, Kasun S. Athukorala Arachchige, Jack K. Clegg, Jason L. Dutton
Abstract
It has been previously proposed that pyridines can activate PhICl2 by displacing a chloride and forming the [PhI(Pyr)(Cl)]+ cation as a reactive intermediate. Here we show that pyridine does not displace chloride, but rather forms a weak complex with the iodine via halogen bonding along the C-I bond axis. This interaction is interrogated by NMR, structural, charge density, and theoretical investigations, which all indicate that pyridine does not activate PhICl2 as proposed.
Topics & Concepts
PyridineChemistryMedicinal chemistryFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisCrystallography and molecular interactions