Halogen Bonding Helicates Encompassing Iodonium Cations

Alan Vanderkooy; Arvind Kumar Gupta; Tamás Földes; Sofia Lindblad; Andreas Orthaber; Imre Pápai; Máté Erdélyi

doi:10.1002/anie.201904817

Halogen Bonding Helicates Encompassing Iodonium Cations

Alan Vanderkooy, Arvind Kumar Gupta, Tamás Földes, Sofia Lindblad, Andreas Orthaber, Imre Pápai, Máté Erdélyi^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

69 Citations (Scopus)

Abstract

The first halonium-ion-based helices were designed and synthesized using oligo-aryl/pyridylene-ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X-ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4-penten-1-ol.

Original language	English
Pages (from-to)	9012-9016
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	27
Early online date	5 Jun 2019
DOIs	https://doi.org/10.1002/anie.201904817
Publication status	Published - 5 Jul 2019

Keywords

3c–4e bonds
halocyclization
halogen bonds
helices
iodonium ions

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AU - Vanderkooy, Alan

AU - Gupta, Arvind Kumar

AU - Földes, Tamás

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AU - Orthaber, Andreas

AU - Pápai, Imre

AU - Erdélyi, Máté

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AB - The first halonium-ion-based helices were designed and synthesized using oligo-aryl/pyridylene-ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X-ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4-penten-1-ol.

KW - 3c–4e bonds

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KW - helices

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Halogen Bonding Helicates Encompassing Iodonium Cations

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