Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes

Tetrahedron, Год журнала: 2025, Номер 173, С. 134467 - 134467

Опубликована: Янв. 12, 2025

Язык: Английский

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Recent Advances in Electrochemical Cascade Cyclization Reactions

Synthesis, Год журнала: 2023, Номер 55(18), С. 2911 - 2925

Опубликована: Фев. 20, 2023

Abstract This review highlights recent progress in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, such as pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-α]pyridines, imidazoles, etc. The works included herein are introduced two major sections heterocycle construction carbocycle reactions, covering reported from 2012 to 2022. 1 Introduction 2 Electrochemical Cascade Cyclization Synthesis Heterocycles 2.1 Pyridines, Quinolines, Phenanthridines, Cinnolines 2.2 1,4-Dihydroquinolines, Hexacyclic Sulfonamides, Thiazines 2.3 Hydroisoquinolinones Hydroquinolinones 2.4 Quinazolin-4(3H)-ones 2.5 4H-3,1-Benzoxazines 2.6 Oxindoles 2.7 Indolines Indoles 2.8 Imidazo[1,5-α]pyridines Imidazoles 2.9 Imidazolones, Imidazolidinones, Oxazolones, Oxazolidinones 2.10 Benzoxazoles, Oxazolines, Isoxazolines 2.11 Furans Dihydrofurans 2.12 Indolizines, Pyrazoles, Triazolium Inner Salts 2.13 Sulfonated Benzothiophenes, Thiazoles, Dihydrothiazoles, 1,3,4-Thiadiazoles 2.14 Lactones 3 Construction Carbocycles 3.1 Carbon Polycycles Spiroindenes 3.2 Difluoroacyl (Hetero)arenes Indenones 4 Conclusion

Язык: Английский

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The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

ACS Omega, Год журнала: 2022, Номер 7(44), С. 39531 - 39561

Опубликована: Окт. 27, 2022

Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which broadly used in organic synthesis work active pharmaceutical substances. Generally, considered good building blocks show powerful value a diverse range of reactions construct C–S bonds C–C bonds, even C–N sulfur, carbon, nitrogen sources, respectively. As profound synthetic tool, the electrosynthesis method was recently achieve efficient green applications hydrazides. Interestingly, many unique novel electrochemical syntheses using radical precursors have been developed, including cascade reactions, functionalization heterocycles, well continuous flow combining with since 2017. Accordingly, it is necessary specifically summarize recent developments only more deeply understand better design reactions. Herein, research 2017 reviewed detail based on chemical structures products reaction mechanisms.

Язык: Английский

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Synthesis of meta-Sulfonylpyridines via Copper(II)-Catalyzed Cascade Sulfonylation/Cyclization/Aromatization of Tertiary Enamides with Sulfonylhydrazides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 5, 2025

A copper(II)-catalyzed radical cascade reaction of N-propargyl enamides with sulfonyl hydrazides was developed, which provided an unprecedented method for the direct synthesis meta-sulfonylpyridines in high efficiency good functional group compatibility and simple operation. Mechanistic studies indicated that this tandem process might be composed addition, intramolecular cyclization oxidative aromatization.

Язык: Английский

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Recent advances in electrooxidative radical transformations of alkynes

Science China Chemistry, Год журнала: 2022, Номер unknown

Опубликована: Дек. 12, 2022

Abstract During the past few years, electrochemical oxidative reactions through radical intermediates have emerged as an environmentally-benign, powerful platform for facile formation of C–E (E = C, N, S, Se, O and Hal) bonds single-electron-transfer (SET) processes at electrodes. Functionalized unsaturated molecules unusual structural motifs can, instance, be directly constructed under exceedingly mild reaction conditions initial attack onto alkynes. This minireview highlights recent advances in electrooxidation until June 2022, with a particular focus on additions

Язык: Английский

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Selective Electrochemical Synthesis of 9-Aryl-10-sulfonyl Substituted Phenanthrene from Alkynes and Sulfonyl Hydrazides

Organic Letters, Год журнала: 2022, Номер 24(50), С. 9322 - 9326

Опубликована: Дек. 9, 2022

An efficient electrochemical synthesis of sulfonated phenanthrenes via the reaction internal alkynes with sulfonyl hydrazides has been established. The protocol does not require a metal catalyst or external oxidants, providing green and mild route to functionalized phenanthrenes. Moreover, compatibility various functional groups decagram-scale experimental conditions demonstrate practicality strategy.

Язык: Английский

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Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2296 - 2305

Опубликована: Фев. 2, 2023

A simple and efficient electrochemical sulfonylation of organoboronic acids with sodium arylsulfinate salts has been reported for the first time. variety aryl, heteroaryl, alkenylsulfones were obtained in good to excellent yields via a various arylboronic acids, heterocyclic boronic or alkenylboronic at room temperature 5 h under catalyst-free additive-free conditions. plausible mechanism proposed based on radical-trapping CV control experiments.

Язык: Английский

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Electrochemical Reduction of Benzo[b]thiophene 1,1‐Dioxides with HFIP as Hydrogen Donor^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(6), С. 585 - 591

Опубликована: Ноя. 2, 2023

Comprehensive Summary A straightforward electrochemical reduction of benzo[ b ]thiophene 1,1‐dioxides with HFIP as the hydrogen donor has been reported in an undivided cell under metal‐free conditions. Moreover, tolerance various functional groups and scaled‐up experiments showed practicability potential applications this methodology.

Язык: Английский

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Non-Friedländer Route to Diversely 3-Substituted Quinolines through Au(III)-Catalyzed Annulation Involving Electron-Deficient Alkynes

Organic Letters, Год журнала: 2023, Номер 25(48), С. 8756 - 8760

Опубликована: Ноя. 28, 2023

Gold(III)-catalyzed annulation of electron-deficient alkynes and 2-amino-arylcarbonyls provides general modular one-step access to a broad scope quinoline products. This highly selective reaction is useful alternative the classic Friedländer synthesis, which requires harsh conditions. In contrast, developed method works under relatively mild PicAuCl2-catalyzed conditions exhibits high functional group tolerance (40 examples; yields ≤96%). Another feature approach versatility toward other alkynes. Alkynylsulfones, alkynylcarbonyls, alkynylphosphonates, propiolonitriles, trifluoromethylated can be used as starting materials for preparation quinolines diversely substituted at position 3. On basis experimental data, we proposed mechanism in gold(III) functions strong electrophilic activator C≡C bond carbonyl group. The synthetic potential presented additionally illustrated by practical postmodifications obtained compounds, including two-step synthesis interpirdine, potent drug candidate.

Язык: Английский

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An electrochemical method for direct sulfonylation of BODIPYs under green conditions

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(2), С. 477 - 483

Опубликована: Дек. 1, 2023

An environmentally benign electrochemical approach has been developed for the construction of β-sulfonylated BODIPYs by using sulfonylhydrazide as sulfonyl source.

Язык: Английский

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