Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6117 - 6125

Published: April 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Language: Английский

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Electrochemical Multicomponent Cascade Reaction for the Synthesis of Selenazol-2-amines with Elemental Selenium

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4113 - 4119

Published: March 6, 2024

The first example of an electrochemical multicomponent synthesis selenium-containing compounds with inexpensive and abundant elemental selenium as the selenating reagent was developed. A variety selenazol-2-amines were constructed in high yields good functional group tolerance under metal-free chemical oxidant-free conditions.

Language: Английский

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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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Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)

Published: Jan. 20, 2024

Abstract A practical and mild electrochemical dehydrogenative regioselective cyclization method has been established for the synthesis of 4‐pyrrolin‐2‐ones using 3‐aza‐1,5‐dienes 1,3‐dicarbonyl compounds as substrates. This protocol is catalyst‐free, metal‐free, does not require oxidizing agents. It exhibits wide substrate compatibility can be easily scaled up to gram scale.

Language: Английский

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Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

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Manganese(III)-Mediated Selective Cascade Phosphorylation-Cyclization of Tertiary Enamides for the Synthesis of Multi-Substituted 3-Phosphorylpyridines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

A novel regioselective manganese(III)-mediated radical cascade cyclization of N-propargyl enamides with various H-phosphine oxides, H-phosphinates and H-phosphonates was developed. Mechanistic studies show that the reaction is mainly composed selective addition phosphonyl to C≡C bond intramolecular 6-endo-trig vinyl radical. Utilizing this protocol, we successfully synthesized a diverse range 3-phosphorylpyridines in high efficiency good functional group compatibility simple operation.

Language: Английский

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Divergent Synthesis of Polysubstituted 1,2-Dihydropyridines and Pyridines through Manganese-Mediated Radical Cascade Cyclization of Tertiary Enamides

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

A Mn(III)-mediated radical cascade cyclization of N-propargyl enamides with sodium sulfinates was developed. Mechanistic studies indicated that this process is mainly composed the chemoselective addition sulfonyl to C≡C bond and regioselective intramolecular 6-endo-trig cyclization. This protocol provided a powerful method for divergent synthesis diverse polysubstituted meta-sulfonylpyridines or 1,2-dihydropyridines just by varying solvent temperature featuring good functional group compatibility simple operation.

Language: Английский

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Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions

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

Published: April 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Language: Английский

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Visible‐light‐induced Regioselective Selenohydroxylation of Enamine Amides with Diaryl Diselenides

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 26, 2024

Abstract This article reports the synthesis of alpha‐hydroxy‐beta‐seleno amides containing intramolecular hydrogen bonds by selective oxyselenization and double bond cleavage reactions enamine with diaryl diselenides under visible light irradiation. protocol proceeds well to provide 30 desired products yields 37 %–80 % using 12 W blue LED as source room temperature conditions. Moreover, plays a dual role substrate photoactive reagent, oxygen in air participates reaction, thus avoiding extra addition environmentally unfriendly photoctalysts oxidants.

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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