Electrochemical Synthesis of <i>trans</i>-2,3-Disubstituted Aziridines via Oxidative Dehydrogenative Intramolecular C(sp<sup>3</sup>)–H Amination

Wang, Huiqiao; Shi, Jianxue; Tan, Jiajing; Xu, Wenting; Zhang, Sheng; Xu, Kun

doi:10.1021/acs.orglett.9b03641

Cited by 55 publications

(23 citation statements)

References 73 publications

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“…Excluding external oxidants in electrochemical intramolecular oxidative dehydrogenative amination of substrates 28 has been reported [ 53 ] ( Scheme 34 ). The resulting 3-arylated aziridines trans -1a10 were obtained in good yields.…”

Section: Perspective Photo- and Electrochemical Methods In The Synthe...mentioning

confidence: 99%

Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones

Strumfs

Velikijs

Uljanovs

et al. 2022

IJMS

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Highly functionalized aziridines, including compounds with aromatic moieties, are attractive substrates both in synthetic and medical areas of chemistry. There is a broad and interesting set of synthetic methods for reaching these compounds. Aziridination represents the most explored tool, but there are several other more specific, less well-known, but highly promising approaches. Therefore, the current review focuses on recently described or updated ways to obtain 3-arylated aziridines via different non-aziridination-based synthetic methods, reported mainly since 2000. The presented methods belong to two main directions of synthesis, namely, cyclization of open-chain substrates and rearrangement of other heterocycles. Cyclization of open-chain substrates includes the classic Gabriel-Cromwell type cyclization of halogenated substrates with amines, base-promoted cyclization of activated aminoalcohols (or its analogues), and the oxidative cyclization of β-dicarbonyls. Rearrangements of other heterocycles are presented as the Baldwin rearrangement of 4-isoxazolines, the cycloaddition of 1.3-dipoles or dienes to 2H-azirines, and the addition of C- and N-nucleophiles to the double bond of azirines.

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Section: Perspective Photo- and Electrochemical Methods In The Synthe...mentioning

confidence: 99%

Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones

Strumfs

Velikijs

Uljanovs

et al. 2022

IJMS

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“…In 2019, we realized an electrochemical aziridine synthesis via an intramolecular C(sp 3 )−H/N−H oxidative coupling reaction with KI as the mediator (Scheme 34). [28] This intramolecular cyclization was carried out in an undivided cell equipped with platinum electrodes with THF/MeOH as the mixed solvent. The mild reaction conditions resulted in the excellent functional group compatibility.…”

Section: Halogen As the Inner‐sphere Et Mediatorsmentioning

confidence: 99%

Indirect Electrosynthesis with Halogen Ions as Mediators

Lian

Zeng

2021

The Chemical Record

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Organic electrosynthesis has gained increasing research interest as it harvests electric current as redox regents, thereby providing a sustainable alternative to conventional approaches. Compared with direct electrosynthesis, indirect electrosynthesis employs mediator(s) to lower the overpotentials for substrate activation, and enhance the reaction efficiency and functional group compatibility by shifting the heterogenous electron transfer process to be homogenous. As one of the most versatile and cost‐efficient mediators, halogen mediators are always combined with an irreversible halogenation reaction. Thus, the electrochemical reaction between halogen mediators and substrates doesn't directly controlled by the two standard potentials difference. In this account, our recent developments in the area of halogen‐mediated indirect electrosynthesis are summarized. The anodically generated halogen species from halogenide salts have the abilities to undergo electron‐transfer (ET) or hydrogen‐atom‐ transfer (HAT) processes. The reaction features, scopes, limitations, and mechanistic rationalisations are discussed in this account. We hope our studies will contribute to the future developments to broaden the scope of halogen‐mediated electrosynthesis.

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“…The well‐known combination of iodide as a mediator and supporting electrolyte coupled with electrocatalysis was insightfully explored by Xu and co‐workers [26] for the synthesis of trans ‐2,3‐disubstituted aziridines (Scheme 15). The reaction provides only trace product in the absence of the iodide, signifying that the reaction does not proceed using direct electrolysis mode.…”

Section: Non‐metallic Redox Mediator Merged With Electrosynthesismentioning

confidence: 99%

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

2021

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Embracing sustainable green methodologies and techniques in chemical transformations has always been in the limelight to the synthetic community. Electrosynthesis has emerged as a powerful, sustainable synthetic tool for molecular synthesis exploiting inexpensive electricity in place of sacrificial chemical oxidizing/reducing reagents. Herein, recent advances in the incorporation of transition metal‐free redox mediators in electrosynthesis for the construction of C−N bonds are outlined. Furthermore, conjugation of this strategy with flow catalysis allows easy scale up of the synthesis of molecular assembly. This comprehensive Review provides an overview of metal‐free mediated electro‐construction of C−N bonds, focusing on the reaction mechanisms involved and its synthetic applications.

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Electrochemical Synthesis of trans-2,3-Disubstituted Aziridines via Oxidative Dehydrogenative Intramolecular C(sp³)–H Amination

Cited by 55 publications

References 73 publications

Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones

Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones

Indirect Electrosynthesis with Halogen Ions as Mediators

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

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Electrochemical Synthesis of trans-2,3-Disubstituted Aziridines via Oxidative Dehydrogenative Intramolecular C(sp3)–H Amination

Cited by 55 publications

References 73 publications

Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones

Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones

Indirect Electrosynthesis with Halogen Ions as Mediators

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

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Product

Resources

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Electrochemical Synthesis of trans-2,3-Disubstituted Aziridines via Oxidative Dehydrogenative Intramolecular C(sp³)–H Amination