On the activation of PhICl2 with pyridine

Article

Poynder, Tiffany B., Orue, Analia I. Chamorro, Tania, Sharp-Bucknall, Lachlan, Flynn, M., Wilson, David J. D., Arachchige, K., Clegg, J.K. and Dutton, Jason L.. 2021. "On the activation of PhICl2 with pyridine." Chemical Communications. 57 (40), pp. 4970-4973. https://doi.org/10.1039/d1cc01567b
Article Title

On the activation of PhICl2 with pyridine

ERA Journal ID1319
Article CategoryArticle
AuthorsPoynder, Tiffany B., Orue, Analia I. Chamorro, Tania, Sharp-Bucknall, Lachlan, Flynn, M., Wilson, David J. D., Arachchige, K., Clegg, J.K. and Dutton, Jason L.
Journal TitleChemical Communications
Journal Citation57 (40), pp. 4970-4973
Number of Pages4
Year2021
PublisherThe Royal Society of Chemistry
Place of PublicationUnited Kingdom
ISSN1359-7345
1364-548X
Digital Object Identifier (DOI)https://doi.org/10.1039/d1cc01567b
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.

Keywordsbenzene derivative; iodine; iodobenzene dichloride; pyridine; unclassified drug
ANZSRC Field of Research 2020340503. Organic chemical synthesis
Public Notes

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Byline AffiliationsLa Trobe University
University of Queensland
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