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Halogen Bonding Helicates Encompassing Iodonium Cations
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. (Erdélyi group)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.ORCID iD: 0000-0002-8969-1236
Hungarian Acad Sci, Inst Organ Chem, Res Ctr Nat Sci, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary;Kings Coll London, Dept Chem, London SE1 1DB, England.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. (Erdélyi group)
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 27, p. 9012-9016Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019. Vol. 58, no 27, p. 9012-9016
Keywords [en]
3c-4e bonds, halocyclization, halogen bonds, helices, iodonium ions
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-391952DOI: 10.1002/anie.201904817ISI: 000476691200005PubMedID: 31074942OAI: oai:DiVA.org:uu-391952DiVA, id: diva2:1346448
Funder
Swedish Research Council Formas, 2017-01173Available from: 2019-08-28 Created: 2019-08-28 Last updated: 2019-08-28Bibliographically approved

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Vanderkooy, AlanGupta, Arvind KumarLindblad, SofiaOrthaber, AndreasErdélyi, Máté

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