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Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 6
2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 53, 13249-13258 p.Article in journal (Refereed) Published
Abstract [en]

A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.

Place, publisher, year, edition, pages
2017. Vol. 23, no 53, 13249-13258 p.
Keyword [en]
aryl ethers, arynes, hypervalent iodine, mechanistic study, oxidation
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-148082DOI: 10.1002/chem.201703057ISI: 000411357000038PubMedID: 28792102OAI: oai:DiVA.org:su-148082DiVA: diva2:1152334
Available from: 2017-10-24 Created: 2017-10-24 Last updated: 2017-10-24Bibliographically approved

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