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

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5824 - 5831

Published: Jan. 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.

Language: Английский

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Cyclization of Azobenzenes Via Electrochemical Oxidation Induced Benzylic Radical Generation

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 5978 - 5983

Published: Aug. 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.

Language: Английский

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Electrochemical N–H Methylsulfoxidation of Sulfoximines with DMSO

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 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.

Language: Английский

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Electrooxidation-induced arylsulfonylation of xanthene derivatives with DABSO as an SO2 surrogate

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An electrochemical redox C(sp3)-H arylsulfonylation of xanthenes has been developed using aryl diazonium tetrafluoroborates and DABSO as the arylsulfone source. This radical reaction proceeds via formation arylsulfonyl radicals from between DABSO, followed by a cross-coupling process. Notably, occurs in absence any catalyst or external oxidant, providing efficient sulfonylation with broad functional group compatibility.

Language: Английский

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

Organic Letters, Journal Year: 2023, Volume and Issue: 25(37), P. 6919 - 6924

Published: Sept. 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.

Language: Английский

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

RSC Advances, Journal Year: 2024, Volume and Issue: 14(1), P. 154 - 159

Published: Jan. 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.

Language: Английский

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

Molecules, Journal Year: 2023, Volume and Issue: 28(16), P. 6139 - 6139

Published: Aug. 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.

Language: 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, Journal Year: 2024, Volume and Issue: 89(7), P. 4673 - 4683

Published: March 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.

Language: 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, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 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.

Language: Английский

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The Road to Green Efficiency: Exploration of multicomponent reactions from transition metal catalysis to no catalyst conditions

Reaction Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 10(3), P. 500 - 510

Published: Dec. 20, 2024

Multicomponent reactions (MCRs) have become excellent tools for synthesizing complex and high-value molecules. This minireview highlights recent progresses in MCRs classified by the type of catalysts to offer a better deeper understanding.

Language: Английский

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