Zweihundert Jahre Iodforschung: ein interdisziplinärer Überblick über die derzeitige Forschung

Küpper, Frithjof C.; Feiters, Martin C.; Olofsson, Berit; Kaiho, Tatsuo; Yanagida, Shozo; Zimmermann, Michael; Carpenter, Lucy J.; Luther, George W.; Lu, Zunli; Jönsson, Mats; Kloo, Lars

doi:10.1002/ange.201100028

Cited by 27 publications

(6 citation statements)

References 262 publications

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“…To solve this problem, molecular iodine or iodine‐containing reagents are most suitable. Iodine is a widely used oxidizing agent, especially for the oxidation of alcohols and aldehydes to esters, nitriles and amides [1,2] . The most widespread direction of iodination of organic compounds in recent years has been the use of molecular iodine or iodide anion in combination with effective oxidizing agents.…”

Section: Introductionmentioning

confidence: 99%

Iodination of Substituted Alkynes in the Presence of Cadmium(II) Acetate

Sargsyan,

Balyan,

Pogosyan

et al. 2024

ChemistrySelect

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A convenient and selective method for the preparation of substituted iodoalkynes, iodoalkenes based on the interaction of propargylic compounds with iodine in the presence of readily available cadmium (II) acetate in some solvents was developed. The highest yields of iodoalkynes and iodoalkenes were recorded using DMSO as the solvent. An excess of the alkylpropargyl substrate unambiguously led to iodolkynes. By varying the reaction conditions using a twofold excess of iodine in DMSO, methanol or ethanol it was possible to achieve a one‐pot preparation of triiodoalkenes. The interaction of iodine with propargyl substrates could be represented in two ways: formation and further nucleophilic transformation of the iodonium complex under the influence of the acetate ion and generation of π‐coordinated species and elimination of acetic acid.

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Section: Introductionmentioning

confidence: 99%

Iodination of Substituted Alkynes in the Presence of Cadmium(II) Acetate

Sargsyan,

Balyan,

Pogosyan

et al. 2024

ChemistrySelect

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“…As an oxidant of group VIIa, molecular iodine is distinguished by its low toxicity, operational simplicity and mild oxidation strength compared to other halogens. 3,4 As an environmentally benign oxidizing agent, molecular iodine has been used in various organic reactions. [5][6][7][8][9] It is known that secondary alcohols are readily converted into ketones, while primary alcohols can be first oxidized into the aldehydes and further into the carboxylic acids or their derivatives.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of alcohols to carbonyl compounds with molecular iodine in the presence of potassium tert-butoxide

Luo¹,

Nan²,

Yu³

et al. 2014

Arkivoc

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An efficient protocol for the oxidation of alcohols to carbonyl compounds with molecular iodine and potassium tert-butoxide is described. Various primary and secondary alcohols were converted to the corresponding aldehydes and ketones in high yields. The oxidation of 2-phenylethanol produced an "abnormal" acetalic ketone. The readily availability of starting materials, convenient synthetic procedure, operational simplicity, mild reaction conditions, and high yields makes this protocol a competitive alternative in the synthesis of ynones and ketones as well as aryl aldehydes.

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“…[1] Stereoselective iodocyclization is apowerful synthetic tool for generating iodine-functionalized cyclic compounds,a nd this has been widely applied using chiral substrates and in the total synthesis of natural products. [1] Stereoselective iodocyclization is apowerful synthetic tool for generating iodine-functionalized cyclic compounds,a nd this has been widely applied using chiral substrates and in the total synthesis of natural products.…”

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confidence: 99%

Catalytic Asymmetric Iodocyclization of N‐Tosyl Alkenamides using Aminoiminophenoxy Copper Carboxylate: A Concise Synthesis of Chiral 8‐Oxa‐6‐Azabicyclo[3.2.1]octanes

et al. 2015

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A newly developed aminoiminophenoxy copper carboxylate (L7-Cu-OAc)-catalyzed asymmetric iodocyclization of N-Tosyl alkenamides gave O-cyclized products in good yields with high enantioselectivity. From the O-cyclized products, a skeletal transformation was succeeded in the synthesis of biologically important chiral 8-oxa-6-azabicyclo[3.2.1]octanes. DFT calculations suggested that the acetoxy anion of the [L7-Cu-OAc] acts as a base to generate the anion of N-Tosyl alkenamide substrates. The exchanged acetic acid reconstructs a new hydrogen-bonding network between the catalyst and the substrates to accomplish the highly efficient asymmetric O-iodocyclization of N-Tosyl alkenamides.

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Zweihundert Jahre Iodforschung: ein interdisziplinärer Überblick über die derzeitige Forschung

Cited by 27 publications

References 262 publications

Iodination of Substituted Alkynes in the Presence of Cadmium(II) Acetate

Iodination of Substituted Alkynes in the Presence of Cadmium(II) Acetate

Oxidation of alcohols to carbonyl compounds with molecular iodine in the presence of potassium tert-butoxide

Catalytic Asymmetric Iodocyclization of N‐Tosyl Alkenamides using Aminoiminophenoxy Copper Carboxylate: A Concise Synthesis of Chiral 8‐Oxa‐6‐Azabicyclo[3.2.1]octanes

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