2017
DOI: 10.1002/slct.201701645
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A Metal‐Free Iodination of Aryl Ethers and Phenols Using I2

Abstract: I2/DMSO mediated method for deprotection and selective iodination of allyl aryl ethers and phenols has been developed. A wide range of allyl aryl ethers and phenols have been efficiently iodinated to the respective iodophenols in one pot.

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Cited by 12 publications
(8 citation statements)
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“…It is known that Tyr is among the most vulnerable amino acid residues to iodination modification, with mono- /di-iodotyrosine being generated as a consequence. Typically, this process requires an auxiliary oxidant, metallic catalyst, or harsh conditions . The phenolic hydroxyl group is believed to be entangled in the process of iodination through the tandem sequence of protonated ketone formation, deprotonation, and enolation equilibrium …”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…It is known that Tyr is among the most vulnerable amino acid residues to iodination modification, with mono- /di-iodotyrosine being generated as a consequence. Typically, this process requires an auxiliary oxidant, metallic catalyst, or harsh conditions . The phenolic hydroxyl group is believed to be entangled in the process of iodination through the tandem sequence of protonated ketone formation, deprotonation, and enolation equilibrium …”
Section: Resultsmentioning
confidence: 99%
“…Typically, this process requires an auxiliary oxidant, metallic catalyst, or harsh conditions. 9 The phenolic hydroxyl group is believed to be entangled in the process of iodination through the tandem sequence of protonated ketone formation, deprotonation, and enolation equilibrium. 10 Tyr(Me/Et) is a naturally occurring amino acid frequently found in peptide therapeutics such as atosiban and carbetocin.…”
Section: ■ Introductionmentioning
confidence: 99%
“…1-Iodo-2-methoxynaphthalene (38). 21 The following compound was obtained according to a modified general procedure A, by using 2-methoxynaphthalene as starting material and NH 4 I (reaction was in reflux overnight). The crude material was purified by flash column chromatography over silica gel with the system (3% EtOAc/Hexane) to afford the product 38 (52 mg, 57%) as a white solid.…”
Section: The Journal Of Organic Chemistrymentioning
confidence: 99%
“…Among the most significant iodination strategies are those involving transition metals such as Ru, In, Pd, Mo, Hg, Fe, Ce, Yb, or Ag . A number of transition-metal-free iodination procedures have also been described using I 2 in combination with 1,4-bis­(tri­phenyl­phos­phonium)-2-butene peroxodisulfate, DMSO, HIO 3 , urea-H 2 O 2 , or NO 2 . An additional strategy consists of the oxidation of iodide salts using the systems NH 4 I/H 2 O 2 , NaI/NaClO 2 , or NaClO 2 /NaI/HCl .…”
Section: Introductionmentioning
confidence: 99%
“…These compounds exhibit extraordinary therapeutic and biological activities, including cytotoxic antibacterial, antioxidant, antiviral, anti-HIV, anticancer, and neuroprotective agents. 2 Moreover, the symmetrically substituted xanthones are being applied for the synthesis of fluorophores and fluorescent dyes. 3 Besides the xanthone derivative persulfated 3,6-(O-b-glucopyranosyl)xanthone was a notable dual inhibitor of FXa (anticoagulant agent) and with the antiplatelet effect.…”
mentioning
confidence: 99%