Issue 40, 2021

On the activation of PhICl2 with pyridine

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.

Graphical abstract: On the activation of PhICl2 with pyridine

Supplementary files

Article information

Article type
Communication
Submitted
23 Mar 2021
Accepted
15 Apr 2021
First published
15 Apr 2021

Chem. Commun., 2021,57, 4970-4973

On the activation of PhICl2 with pyridine

T. B. Poynder, A. I. Chamorro Orué, Tania, L. Sharp-Bucknall, M. T. Flynn, D. J. D. Wilson, K. S. Athukorala Arachchige, J. K. Clegg and J. L. Dutton, Chem. Commun., 2021, 57, 4970 DOI: 10.1039/D1CC01567B

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