Recent Advances in Electrochemical Sulfonylation using Sodium Sulfinates as Sulfonyl Radical Precursors

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(2), P. 105 - 116

Published: Jan. 1, 2024

Abstract: Sodium sulfinates have been widely utilized as sulfonyl radical precursors for preparing a diverse array of value-added sulfur-containing compounds (sulfones, sulfonamides, sulfonates, thiosulfonates, etc.) through S-C, S-N, S-O and S-S bonds formation reactions. Organic electrosynthesis has become an attractive alternative to conventional methods redox reactions because it utilizes electric current instead chemical agents. As such, the electrochemical generation radicals from sodium their applications in organic attracted much attention. In this review, recent advances sulfonylation involving since 2015 were reviewed, along with related reaction mechanisms.

Language: Английский

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Regioselective electrochemical cascade C–H sulfonylation–bromination of indolizines to access difunctionalized indolizines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2306 - 2312

Published: Jan. 1, 2024

Regioselective electrochemical C–H sulfonylation–bromination between indolizines, sodium sulfinates, and KBr has been established in an undivided cell, which serves as both the brominating agent electrolyte.

Language: Английский

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CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1714 - 1755

Published: April 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Language: Английский

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Electrochemical Trifluoromethylalkoxylation of Endocyclic Enamides in Batch and Flow

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2919 - 2925

Published: March 2, 2024

Abstract A regioselective electrochemical oxytrifluoromethylation of endocyclic enamides is reported. The 1,2‐difunctionalization proceeds under mild conditions and employs the inexpensive bench stable Langlois’ reagent. This multicomponent strategy gives access to a wide range α,β‐substituted amines by means various alcohols as nucleophiles in high yields with good functional group tolerance. In addition, an electrochemically induced C−H trifluoromethylation has been developed. continuous flow protocol using commercial microflow reactor was also developed improved reaction performance efficiency over traditional batch versions without any supporting electrolyte.

Language: Английский

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Electrolyte-free electrochemical C–H trifluoromethylation of 2-pyridones under batch and flow conditions

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(19), P. 7388 - 7394

Published: Jan. 1, 2022

An environmentally friendly electrochemical process for the direct trifluoromethylation of 2-pyridones with a broad substrate scope has been developed.

Language: Английский

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Disulfides as versatile starting reagents: effective sulfonylation of alkenes with disulfides under electrochemical conditions

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3559 - 3566

Published: Jan. 1, 2023

The unexpectedly effective use of disulfides as S-partners in electrochemical C–S coupling is demonstrated.

Language: Английский

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Synthesis of β‐Hydroxyselenides via Electrochemical Hydroxyselenenylation of Alkenes with Diselenides and H₂O

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(5)

Published: Feb. 2, 2024

Abstract A practical electrochemical method for the synthesis of β‐hydroxyselenides has been developed under an external oxidant‐free condition at room temperature air from alkenes with diselenides and H 2 O. radical mechanism is proposed this transformation gram‐scale reactions demonstrate practicability reaction.

Language: Английский

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Synthesis of 1,3-diselenyl-dihydroisobenzofurans via electrochemical radical selenylation with substituted o-divinylbenzenes and diselenides

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(14), P. 2813 - 2817

Published: Jan. 1, 2022

An efficient electrochemical method for the direct synthesis of complicated 1,3-diselenyl-dihydroisobenzofurans was developed under external oxidant free conditions at room temperature from substituted o-divinylbenzenes and diselenides. A radical mechanism is proposed this novel practical transformation.

Language: Английский

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Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract Imidazoheterocycles have extensive applications in the pharmaceutical industry and agrochemicals. A comprehensive overview has been provided on current advancements electrochemical functionalization of imidazo‐fused heterocycles, which classified into ten different types reactions. Electrochemical synthesis emerged as a highly effective method for producing organic molecules, especially context sustainable development. Employing electrons traceless oxidant, several C−H reactions heterocycles achieved at either C3 or C5 positions. Electrons may serve reducing agent to synthesize pyridine rings that are partially fully saturated imidazo[1,2‐ ]pyridines. The purpose review is attract interest scientific community promote additional research imidazoheterocycles using methods.

Language: Английский

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Recent advances in metal catalyst- and oxidant-free electrochemical C-H bond functionalization of nitrogen-containing heterocycles

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: Aug. 19, 2022

The C-H functionalization of nitrogen-containing heterocycles has emerged as a powerful strategy for the construction carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds. In order to achieve efficient selective functionalization, electrochemical synthesis attracted increasing attention. Because anodic oxidation is ideal replacing chemical reagents in reactions. This mini-review summarizes current knowledge recent advances since 2017 synthetic utility transformations heterocycles.

Language: Английский

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