Electrochemical N(sp²)–H/C(sp³)–H cross-coupling reaction between sulfoximines and alkylarenes

Green Chemistry, Год журнала: 2024, Номер 26(10), С. 5824 - 5831

Опубликована: Янв. 1, 2024

An electrochemical oxidation-induced amination of simple alkylarenes with sulfoximines as a nitrogen source and 5,6-dimethyl-1 H -benzo[ d ]imidazole catalyst was developed.

Язык: Английский

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Cyclization of Azobenzenes Via Electrochemical Oxidation Induced Benzylic Radical Generation

Organic Letters, Год журнала: 2023, Номер 25(32), С. 5978 - 5983

Опубликована: Авг. 7, 2023

An electrochemical oxidation-induced cyclization of ortho-alkyl-substituted azobenzenes has been developed. The direct benzylic C-H functionalization with respect to could proceed in the absence any catalyst or external chemical oxidant afford a number 2H-indazole derivatives moderate good yields. This protocol enables reuse byproduct same 2H-indazoles, thus significantly reducing pollution discharge synthetic chemistry.

Язык: Английский

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Electrochemical N–H Methylsulfoxidation of Sulfoximines with DMSO

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 16, 2025

Comprehensive Summary The N–H methylsulfoxidation of sulfoximines using DMSO as a methylsulfinyl source, induced by electrochemistry, has been developed. This method is the first example an electrochemical reaction in which serves source. Unlike previous reactions involving substrate, exclusively proceed via radical mechanisms, this follows S‐cation pathway. A wide range N ‐methylsulfinyl were successfully obtained.

Язык: Английский

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Electrochemical 1,3-Alkyloxylimidation of Arylcyclopropane Radical Cations: Four-Component Access to Imide Derivatives

Organic Letters, Год журнала: 2023, Номер 25(37), С. 6919 - 6924

Опубликована: Сен. 11, 2023

Herein, a general electrochemical radical-cation-mediated four-component ring-opening 1,3-alkyloxylimidation of arylcyclopropanes, acetonitrile, carboxylic acids, and alcohols is described, providing facile sustainable approach to quickly construct structurally diverse imide derivatives from easily available raw materials in an operationally simple undivided cell. This metal-catalyst- oxidant-free single-electron oxidation strategy offers green alternative for the formation highly reactive cyclopropane-derived radical cations, this protocol features broad functional group tolerance.

Язык: Английский

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Cascade Electrochemical Aerobic Oxygenation of 2-Substituted Indoles and Electrochemical [5 + 3] Annulation with Amidines: Access to Eight-Membered Benzo[1,3,5]triazocin-6(5H)-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4673 - 4683

Опубликована: Март 13, 2024

The cascade electrochemical C3-selective aerobic oxygenation of 2-substituted indoles and [5 + 3] annulation with amidines through an undivided cell galvanostatic method employing molecular oxygen "electricity" as green oxidants was developed. This protocol provides efficient direct approach to eight-membered benzo[1,3,5]triazocin-6(5H)-ones. Mechanistic studies suggested that two subsequent processes both proceeded radical pathways.

Язык: Английский

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Electrochemical N‐Centered Radical‐Triggered Intramolecular N‐N Coupling for the Cyclization of o‐Aminyl Azobenzenes

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(46)

Опубликована: Авг. 28, 2024

Abstract An electrochemical radical cyclization of o ‐aminyl azobenzenes via N ‐centered generation has been developed for the synthesis benzotriazoles. The bearing a sulfonyl protection on amine readily proceeds in absence any external transition metal catalyst or chemical oxidant, and exhibits good tolerance towards functional groups.

Язык: Английский

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Tuning Benzylic C−H Functionalization of (Thio)xanthenes with Electrochemistry

Molecules, Год журнала: 2023, Номер 28(16), С. 6139 - 6139

Опубликована: Авг. 19, 2023

Here, we report a tunable electrochemical benzylic C-H functionalization of (thio)xanthenes with terminal alkynes and nitriles in the absence any catalyst or external chemical oxidant. The can be well controlled by varying conditions, affording specific coupling products via C-C C-N bond formation.

Язык: Английский

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Electrochemical oxidative cyclization of N-allylamides for the synthesis of CF₃-containing benzoxazines and oxazolines

RSC Advances, Год журнала: 2024, Номер 14(1), С. 154 - 159

Опубликована: Янв. 1, 2024

The introduction of trifluoromethyl (-CF3) groups into compounds is a common synthetic strategy in organic chemistry. Commonly used methods for introducing are limited by harsh reaction conditions, low regioselectivity, or the need excess reagents. In this study, facile electrochemical oxidative and radical cascade cyclization N-(2-vinylphenyl)amides synthesis CF3-containing benzoxazines oxazolines was obtained. This sustainable protocol features inexpensive durable electrodes, wide range substrates, diverse functional group compatibility under transition-metal-free, external-oxidant-free, additive-free can be applied an open environment.

Язык: Английский

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Electrochemical Decarboxylative Alkylation of β-Keto Acids with Phenol Derivatives

Chemical Communications, Год журнала: 2024, Номер 60(10), С. 1329 - 1332

Опубликована: Янв. 1, 2024

An electrochemical method for the decarboxylative alkylation of β-ketoacids with phenol derivatives has been developed.

Язык: Английский

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Electrochemically Benzyl Cation‐Triggered Alkylacetoxylation of Terminal Alkynes and Carboxylic Acids

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2721 - 2727

Опубликована: Май 11, 2024

Abstract A catalyst‐free electrochemical alkylacetoxylation reaction of terminal alkynes with (thio)xanthenes and carboxylic acids is developed. Treating the addition products K 2 CO 3 as a base in methanol affords ketones moderate to good yields. Preliminary experimental computational studies indicate that benzylic cation generated from triggers electrophilic alkynes.

Язык: Английский

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