ArticleChemistry (Weinheim an der Bergstrasse, Germany)2017
Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Metal-FreeOrganic letters · 2023Article
- Cyclic Diaryl λJournal of the American Chemical Society · 2023Article
- Orbital analysis of bonding in diarylhalonium salts and relevance to periodic trends in structure and reactivity.Chemical science · 2022Article
- Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Article
- Concerted Nucleophilic Aromatic Substitution Reactions.Angewandte Chemie (International ed. in English) · 2019Review
- Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions.Angewandte Chemie (International ed. in English) · 2018Article
- Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(spJournal of the American Chemical Society · 2018Article
- Metal-free formal synthesis of phenoxazine.Beilstein journal of organic chemistry · 2018Article
- Diels-Alder cycloadditions ofBeilstein journal of organic chemistry · 2018Article
- Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
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6 authors.
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Abstract
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.
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