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

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8632 - 8640

Опубликована: Июнь 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.

Язык: Английский

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Synthesis of tetrahydroquinoline derivatives via electrochemical hydrocyanomethylation or hydrogenation of quinolines with MeCN

Green Chemistry, Год журнала: 2024, Номер 26(9), С. 5160 - 5166

Опубликована: Янв. 1, 2024

Electrochemical hydrocyanomethylation of quinoline skeletons employing acetonitrile as both a hydrogen resource and cyanomethyl precursor has been described.

Язык: Английский

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Synthesis of 5‐Arylselenyluracils via Bromide‐Catalyzed Selective C(sp²)‐H Selenylation of Uracils

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

Опубликована: Май 28, 2025

Abstract Herein, an efficient method for the synthesis of 5‐arylselenyluracils via bromide‐catalyzed selective C( sp 2 )‐H selenylation uracils using boronic acid and elemental selenium as selenyl source was successfully developed. This proceeded smoothly a series arylboronic acids under metal‐free strong oxidant‐free conditions. protocol offered simple catalytic conditions, high efficiency, good functional group compatibility, easy operation, scalable. Furthermore, mechanistic studies suggested that this transformation possibly undergone radical pathway.

Язык: Английский

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Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr₂ Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization

ChemCatChem, Год журнала: 2024, Номер 16(20)

Опубликована: Июнь 27, 2024

Abstract Herein, a method for the assembly of biologically valuable 3‐selenospiro[4,5]decatrienones through CuBr 2 ‐catalyzed ispo ‐cyclization Se powder, boronic acids, and N ‐( p ‐methoxyaryl)propiolamides has been established. In this protocol, noble transition metal, prefunctionalized selenylation reagent, strong chemical oxidant are not employed. This feature wide substrate scope, good functional group tolerance, easy operation, employing earth‐abundant metal as catalyst green air oxidant. Furthermore, several derivatizations performed to showcase practicability our strategy.

Язык: Английский

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Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 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.

Язык: Английский

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Recent Developments in Selenylation of Alkynes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июль 29, 2024

Abstract Alkynes are simple yet important organic feedstocks. The selenylation of alkynes is able to produce complex selenium‐containing compounds in a facile way. Although there some reviews about the alkynes, most them focus on one specific reaction or what types products that can be obtained. There lack attention given various uses different selenium reagents and their mechanisms. This review mainly focuses recent advances (2013–2023) based diverse reagents. Mechanisms how added work will discussed. Different types, including difunctionalization, Se‐annulation, spiro‐cyclization, C−Se coupling, click recorded this review. regioselectivity achieved through mechanisms, radicals, seleniraniums electrophilic cyclization. We hope it do help for future research area.

Язык: Английский

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Synthesis of naphtho[1,2-b]furan-2-carbaldehydes and naphtho[2,1-b]furan-2-carbaldehydes via electrocatalytic 3,3-rearrangement/cyclization of propargylic aryl ethers under mild conditions

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июнь 1, 2024

An electrocatalytic 3,3-rearrangement/cyclization approach has been developed for the transformation of aryl-substituted propargylic aryl ethers to naphtho[1,2-b]furan-2-carbaldehyde and naphtho[2,1-b]furan-2-carbaldehyde derivatives. The reaction proceeded efficiently under mild conditions in absence metal- chemical-oxidant, yielding desired products with good substrate scope functional group tolerance via a radical pathway. Furthermore, control experiment revealed that phenylselenyl-substituted secondary alcohol might be intermediate, 18O labeling indicated oxygen source product possibly deriving from water. Significantly, further transformations were conducted showcase utility this electrosynthesis strategy.

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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