Electrochemical Synthesis of Isoxazolines: Method and Mechanism

Holman, Samuel David Lee; Fazakerley, Neal J.; Poole, Darren L.; Coe, Diane M.; Berlouis, L.E.A.; Reid, Marc

doi:10.26434/chemrxiv.13480263

Cited by 3 publications

(2 citation statements)

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“…11 Very recently, Reid and co-workers furnished an electrochemical methodology by using aldoxime and other alkenes in a [3+2] cycloaddition approach. 12…”

Section: Table 1 Optimization Of Reaction Conditions ...mentioning

confidence: 99%

Koser’s Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions

Peddinti¹,

Budhwan²,

Rawat³

2023

Synthesis

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A metal- and base-free, robust, and convenient approach for the synthesis of isoxazoline derivatives is reported. This protocol involves 1,3-dipolar cycloaddition between in situ generated nitrile oxides from the corresponding aldoximes using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) and maleimides, styrene and acrylonitrile. The described methodology is very attractive as it is operationally simple, has broad scope, and does not require any base, metal, or other additives.

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“…11 Very recently, Reid and co-workers furnished an electrochemical methodology by using aldoxime and other alkenes in a [3+2] cycloaddition approach. 12…”

Section: Table 1 Optimization Of Reaction Conditions ...mentioning

confidence: 99%

Koser’s Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions

Peddinti¹,

Budhwan²,

Rawat³

2023

Synthesis

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“…The electrochemical method development and mechanistic investigation of isooxazoline synthesis discussed in this work has been conducted primarily on the ElectraSyn 2.0 device. An initial version of this work was deposited in ChemRxiv on 22 December, 2020 [31] …”

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Isoxazolines: Method and Mechanism

Holman

Wills

Fazakerley

et al. 2022

Chemistry A European J

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An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline in an electrochemically enabled regio‐ and diastereoselective reaction with electron‐deficient alkenes. Additionally, in‐situ reaction monitoring methods compatible with electrochemistry equipment have been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time‐course) modelling and density functional theory support a stepwise, radical‐mediated mechanism, and discounts hypothesised involvement of closed shell [3+2] cycloaddition pathways.

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Electrochemical and Spectrometric Study of Reactivity of Orthophthalaldehyde with Hydroxylamine: Mechanistic Considerations

2021

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Orthophthalaldehyde (o‐phthalaldehyde, OPA) is a broadly used biologically, synthetically and analytically significant compound. Its properties are connected with its reactivity towards nucleophiles, namely amines in aqueous – mostly basic – solutions. Since the reaction mechanisms of OPA and amine condensation are complicated, strongly depending on the amine structure and, therefore, a systematic study of this kind of reaction is presented. Structure activity relationships based on amine structure and their application in reaction optimization are reported. The present paper deals with reaction of OPA with hydroxylamine which is monitored electrochemically and spectrometrically. The mechanism was formulated on the basis of detailed analysis of electrochemical behavior, of the interception of the intermediate (phthalaldehyde mono‐oxime) and of the isolation and identification of the main product (1H‐2,3‐benzoxazin‐1‐ol).

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Electrochemical Synthesis of Isoxazolines: Method and Mechanism

Cited by 3 publications

References 0 publications

Koser’s Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions

Koser’s Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions

Electrochemical Synthesis of Isoxazolines: Method and Mechanism

Electrochemical and Spectrometric Study of Reactivity of Orthophthalaldehyde with Hydroxylamine: Mechanistic Considerations

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