Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3543 - 3548

Опубликована: Янв. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Язык: Английский

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Electrochemical Dearomative Spirocyclization

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(9)

Опубликована: Март 15, 2023

Electrochemical dearomative spirocyclization serves as a green and sustainable approach to convert the flat, two-dimension aromatic feedstock into value-added three-dimension spirocyclic architectures. This review highlights recent advances, emphasizes mechanistic discussions, showcases synthetic applications of this emerging versatile powerful transformation.

Язык: Английский

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Silver-Enabled Dearomative Trifluoromethoxylation of Indoles

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(4), С. 2325 - 2332

Опубликована: Янв. 17, 2024

The only known method for the dearomative trifluoromethoxylation of indoles is preliminary, with one substrate successfully undergoing reaction. In this study, we not developed a broadly applicable indole but also achieved divergent by fine-tuning reaction conditions. Under optimized conditions, silver salt and an easily handled OCF3 reagent, various smoothly underwent dearomatization to afford diverse array ditrifluoromethoxylated indolines in 50–84% isolated yields up 37:1 diastereoselectivity, fluorinated trifluoromethoxylated were obtained exclusive trans selectivity. addition, conditions compatible other heteroaromatic rings as well styrene moieties.

Язык: Английский

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Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl‐Oxindoles

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(15), С. 1691 - 1698

Опубликована: Март 19, 2024

Comprehensive Summary A novel electrochemical multicomponent cascade reaction of indole‐tethered alkenes with CF 3 SO 2 Na and n ‐Bu 4 NI has been developed, which enables the rapid assembly spiropyrrolidinyl‐oxindoles in good yields. The experimental results DFT calculations suggest that this proceeds through oxidation Na, radical coupling alkene, spirocyclization, sulfinate, iodide substitution, water coupling. This strategy features mild conditions, easy‐to‐handle reactants, chemical finding not only enriches research contents but also provides a green for construction compared existing methodologies.

Язык: Английский

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Cp₂Fe Mediated Electrochemical Synthesis of Phosphonylated Spirocyclic Indolines via Dearomatization of Indoles

Organic Letters, Год журнала: 2023, Номер 25(21), С. 3956 - 3960

Опубликована: Май 18, 2023

A general and robust strategy for the synthesis of phosphonylated spirocyclic indolines has been developed through Cp2Fe-catalyzed electrochemical dearomaztizaion indoles, which proven challenging to achieve via chemical oxidants. range 3,3-spiroindolines were obtained in moderate good yields with excellent diastereoselectivities. The synthetic application was further illustrated by its easy scalability antitumor activity product.

Язык: Английский

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Electrochemical Dearomative Spirocyclization of N-Acyl Thiophene-2-sulfonamides

Organic Letters, Год журнала: 2022, Номер 24(34), С. 6321 - 6325

Опубликована: Авг. 22, 2022

The Friedel–Crafts type alkylation of C2-tethered thiophenes has been reported to be nonregioselective. Taking advantage the highly regioselective 5-exo-trig spirocyclization an electrochemically generated amidyl radical, we have unraveled electrochemical dearomative N-acyl thiophene-2-sulfonamides. Various nucleophilic agents, including carboxylates, alcohols, and fluoride, are readily incorporated afford remotely functionalized spirocyclic dihydrothiophenes, their novel scaffolds shown exhibit promising antitumor activities.

Язык: Английский

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Metal-Free Electrochemical Oxidative Difluoroethylation/Cyclization of Olefinic Amides To Construct Difluoroethylated Azaheterocycles

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(3), С. 1875 - 1883

Опубликована: Янв. 20, 2023

A new strategy of electrochemical oxidative difluoroethylation to generate difluoroethyl radical with sodium difluoroethylsulfinate (DFES-Na) has been reported for the first time. The method allows quick access a variety valuable difluoroethylated azaheterocycles including oxindoles and isoquinoline-1,3-diones via tandem difluoroethylation/cyclization in moderate good yields. cyclopropyldifluoromethylation N-arylacrylamides also works well using this strategy. Moreover, capture cyclic voltammetry (CV) experiments are carried out determine proposed mechanism.

Язык: Английский

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Electrooxidative α-hydroxymethylation of ketones with dimethylformamide as the carbon source

Green Chemistry, Год журнала: 2023, Номер 25(8), С. 3016 - 3020

Опубликована: Янв. 1, 2023

We report the electrocatalytic α-hydroxymethylation of ketones using DMF as carbon source at room temperature in air a conversion that proceeds without need for toxic and expensive chemical oxidants or metal catalysts.

Язык: Английский

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Electrochemical Access to Difluoromethyl Groups: An Overview of Scope, Mechanisms, and Challenges

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6826 - 6851

Опубликована: Апрель 14, 2025

Язык: Английский

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Ball‐Milling‐Promoted Copper‐Catalyzed Solid‐State Radical C–H Difluoroalkylation Reactions

ChemistryEurope, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

A mechanochemical strategy for promoting copper‐catalyzed solid‐state radical C–H difluoroalkylation reactions has been devised. Compared to traditional solution‐based methods, this mechanoredox approach offers enhanced ease of handling, greater cleanliness, and improved sustainability the synthesis difluoroalkylated indoles, which constitute crucial structural motifs in contemporary drug discovery. The underlying reaction mechanism is investigated through meticulous step‐by‐step control experiments that highlighted substantial influence conditions. versatility protocol demonstrated by its applications complex natural products derivatives.

Язык: Английский

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