Regio- and Stereoselective Synthesis of 3-Selenylazaflavanones and 3-Selenylflavanones via Electrochemically Facilitated Selenylation Cascade

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4074 - 4084

Published: Feb. 23, 2024

Herein, an oxidant- and metal-free electrochemical selenylation reaction of chalcones with diselenides for the synthesis 3-selenylazaflavanones 3-selenylflavanones at room temperature was reported. The method proceeded under mild conditions, exhibited a broad substrate scope, provided selenylated products in moderate to excellent yields high regio- stereoselectivity. could also be readily scaled up efficiency. Detailed mechanistic studies through control experiments disclosed that selenium-based radical might participate this transformation.

Language: Английский

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Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8632 - 8640

Published: June 6, 2024

Herein, we disclosed a highly efficient pathway toward 3-selenylated chromone derivatives via electrocatalytic cascade selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amendable to scale-up the reaction. Additionally, preliminary experiments revealed that reaction probably proceeded cation instead radical pathway.

Language: Английский

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Controllable Construction of Vinyl Sulfones and β‐Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1367 - 1372

Published: Feb. 23, 2024

Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions. electrochemical C—H proceeded smoothly to afford ( E )‐vinyl sulfones good selectivity in an undivided cell without external oxidant. While aerobic trifunctionalization occurred presence KI air, which provides β ‐keto selenosulfones via formation C—O, C—S, and C—Se bonds one‐pot. Following control experiments, a plausible mechanism is proposed rationalize experimental results.

Language: Английский

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Cathodic tandem alkylation/dearomatization of heterocycles enabled by Al-facilitated carbonyl deoxygenation

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 25, 2025

Language: Английский

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A Comprehensive Review of Magnetic Nanocatalysts for C−S, C−Se Bond Formation

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Abstract This review manuscript examines magnetic nanocatalysts and their pivotal role in forming carbon‐sulfur (C−S) carbon‐selenium (C−Se) bonds. The study delves into the latest advancements synthesis, characterization, application of nanocatalysts, highlighting unique advantages, including enhanced catalytic activity, superior selectivity, easy recovery through separation, which align with principles green chemistry. Through a critical analysis recent research findings, this also explores mechanistic pathways facilitated by these offering insights operational efficiency potential for recyclability. aims not only to catalog current achievements burgeoning field but identify challenges propose future directions developing more efficient, sustainable, versatile systems C−S C−Se bond formation. By encompassing broad spectrum ranging from bare magnets functionalized composite materials, is comprehensive resource researchers engaged organic catalysis, sustainable

Language: Английский

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Direct C-H Selenylation of (Benz)Imidazole and related heterocycles via Cooperative Action of Palladium and Silver Catalyst

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134667 - 134667

Published: April 1, 2025

Language: Английский

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Electrochemically Driven para‐Selective C(sp²)−H Alkylation Enabled by Activation of Alkyl Halides without Sacrificial Anodes

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(25)

Published: Feb. 23, 2024

Abstract With alkyl halides (I, Br, Cl) as a coupling partner, an electrochemically driven strategy for para ‐selective C(sp 2 )−H alkylation of electron‐deficient arenes (aryl esters, aldehydes, nitriles, and ketones) has been achieved to access diverse alkylated in one step. The reaction enables the activation absence sacrificial anodes, achieving formation )‐C(sp 3 ) bonds under mild electrolytic conditions. utility this protocol is reflected high site selectivity, broad substrate scope, scalable.

Language: Английский

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Electrochemical selenylative ipso-Annulation of N-benzylacrylamides to seleno-azaspiro[4.5]decadienones

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(30), P. 6141 - 6148

Published: Jan. 1, 2024

Construction of seleno azaspiro[4.5]decadienones using an electrochemical approach is achieved via domino selenylation/ ipso -annulation.

Language: Английский

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Electroreduction Reactions Mediated by Organic Molecules: Recent Advances and Applications

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Aug. 27, 2024

Abstract Electroreduction is an important aspect of organic electrochemistry. Its chemistry does not require the addition additional reductants, making it effective alternative to various traditional reduction reactions. Among them, organo‐mediated electroreduction recognized as a promising approach. Organo‐mediators can be reduced directly at cathode form reactive radical anions that subsequently reduce substrate via electron transfer ( ET ) initiate reaction being investigated. typically have more positive potential, and their role in whole similar catalysts. Their transforms process from original heterogeneous into homogeneous one. Organo‐mediated effectively avoid over‐electrolysis product electrode intolerance sensitive substrates or functional groups during electrolysis, thereby preventing occurrence side It also prevent excessive consumption reagents electrical energy while promoting achieve higher completely different selectivity. Considering advantages this type reaction, review will provide detailed description reactions mediated by molecules recent years elucidate mechanism organo‐mediators transformations.

Language: Английский

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Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides

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

Published: Oct. 19, 2024

Abstract Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization ynamides was disclosed. A series diaryl diselenides, dialkyl and heteroaryl‐substituted tolerated in this protocol delivered 4‐selenyloxazolones 28–83% yields. The scale‐up reaction the oxidation performed to showcase practicability method. Furthermore, mechanistic experiments indicated that a cationic pathway instead radical probably involved.

Language: Английский

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