2017
DOI: 10.1016/j.tetlet.2017.07.088
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A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine

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Cited by 22 publications
(12 citation statements)
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“…On the basis of the above experiments and the previous investigations, a plausible reaction mechanism was outlined in Scheme . Initially, I – ions are electro-oxidized at the anode to form a reactive iodide radical or I 2 . , At the same time, phenylhydrazine easily reacts with paraformaldehyde to produce intermediate 1-methylene-2-phenylhydrazine 2a .…”
Section: Resultsmentioning
confidence: 86%
See 1 more Smart Citation
“…On the basis of the above experiments and the previous investigations, a plausible reaction mechanism was outlined in Scheme . Initially, I – ions are electro-oxidized at the anode to form a reactive iodide radical or I 2 . , At the same time, phenylhydrazine easily reacts with paraformaldehyde to produce intermediate 1-methylene-2-phenylhydrazine 2a .…”
Section: Resultsmentioning
confidence: 86%
“…Then the radical B can be converted to a resonance structural radical C . On the other hand, the alcohol can be chemically oxidized to aldehyde at room temperature with the help of I 2 electrogenerated at the anode . Subsequently, the aldehyde reacts with NH 3 resulting from the electroreduction of NH 4 + ions at the cathode to form aldimine intermediate D , followed by the reaction with I 2 to generate an N -iodo aldimine intermediate E .…”
Section: Resultsmentioning
confidence: 99%
“…ACT (2) can also be oxidized using iodine as the secondary oxidant in a biphasic reaction with collidine (Scheme 18, III). 61 This catalytic system is of particular interest because no overoxidized dimeric esters were observed for the aliphatic substrates (9e). Scheme 17 Oxidation of alcohols with 82 containing a nitrate counterion that expands the scope of the oxidation.…”
Section: Oxidation Of Alcoholsmentioning
confidence: 99%
“…A company is using the process to manufacture 3,3‐dimethylbutanal, a feedstock for an approved N ‐alkyl derivative of a sweetener . Similarly, scholars in Japan introduced the advantageous use of high volumetric efficient NaOCl⋅5 H 2 O crystals in place of conventional aqueous NaOCl, and Chernyshev and co‐workers discovered that elemental iodine can replace hypochlorite as primary oxidant (with a catalytic amount of an alkyl‐substituted pyridine) …”
Section: Introductionmentioning
confidence: 99%
“…[5] Similarly,s cholars in Japan introduced the advantageous use of high volumetric efficient NaOCl·5 H 2 O crystalsi np lace of conventional aqueous NaOCl, [6] andC hernyshev and co-workers discovered that elemental iodine can replace hypochlorite as primary oxidant( with ac atalytic amount of an alkyl-substituted pyridine). [7] Concomitantly,a iming at avoiding loss of the valued (and moderately toxic) catalyst, al arge research effortsh ave been devoted to heterogenize the TEMPOm oiety by supporting it onto organic,i norganic and hybrid organic-inorganic materials. Ar eview [8] by Megiel encompasses tens of different examples that span from 1995 Endo's surfaced erivatization of ultrafine silica and ferrite, [9] through recent covalent graftingo fn itroxyl radicals onto graphene.…”
Section: Introductionmentioning
confidence: 99%