Electrochemical synthesis of selenyl imidazo[2,1-b]thiazinones via three-component reactions

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5813 - 5819

Опубликована: Янв. 1, 2024

In this paper, we have developed an efficient strategy for the concise synthesis of diverse selenyl imidazo[2,1- b ]thiazinones via electrochemical oxidative three-component tandem reactions in absence transition metals, and oxidants.

Язык: Английский

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Electrochemical Enabled Cascade Phosphorylation of N−H/O−H/S−H Bonds with P−H Compounds: An Efficient Access to P(O)‐X Bonds

Chemistry - A European Journal, Год журнала: 2021, Номер 27(60), С. 14931 - 14935

Опубликована: Авг. 27, 2021

An electrochemical three component cascade phosphorylation reaction of various heteroatoms-containing nucleophiles including carbazoles, indoles, phenols, alcohols, and thiols with Ph2 PH has been established. Electricity is used as the "traceless" oxidant water air are utilized "green" oxygen source. All kinds structurally diverse organophosphorus compounds P(O)-N/P(O)-O/P(O)-S bonds assembled in moderate to excellent yields (three categories products, 50 examples, up 97 % yield). A tentative free radical course put forward rationalize procedure.

Язык: Английский

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Palladium‐Catalyzed Stereoselective Intramolecular Heck Dearomative Silylation of Indoles

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(4), С. 909 - 913

Опубликована: Янв. 11, 2022

Abstract A palladium‐catalyzed stereoselective intramolecular Heck dearomative of indoles with silyl termination has been developed. type tetracyclic indoline derivatives containing silicon were prepared, involving N ‐(2‐bromobenzoyl)indoles and silylboronates. This protocol not only led to a broad substrate scope in acceptable yields but also could be scaled up gram quantities as well further synthetic transformation. magnified image

Язык: Английский

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Electrochemical Oxidation‐Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(16), С. 2735 - 2740

Опубликована: Июль 1, 2022

Abstract A metal‐ and exogenous‐oxidant‐free oxidation‐induced oxyphosphorylation of alkenes alkynes with water for β‐ketophosphonates has been developed through the radical coupling under electrochemical conditions. This protocol is compatible a wide range alkenes, alkynes, diarylphosphorus derivatives, enables gram‐scale synthesis β‐ketophosphonates. The mechanistic study revealed that P radicals were generated via hydrogen atom transfer (HAT) event jointly mediated by tetrabutylammonium acetate anode oxidation process. magnified image

Язык: Английский

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Copper-Catalyzed Phosphorylation of N,N-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 6224 - 6236

Опубликована: Апрель 20, 2022

An efficient copper-catalyzed aerobic oxidative cross-dehydrogenative coupling reaction for the synthesis of multisubstituted phosphorylhydrazides from N,N-disubstituted hydrazines and hydrogen phosphoryl compounds is accomplished. The proceeds under mild conditions without addition any external oxidants bases. This work reported here represents a direct P(═O)-N-N bond formation with advantages being operationally simple, good functional group tolerance, high atom step economy. Furthermore, selected exhibit potential inhibitory activity against tumor cells, which can be used in field screening anticancer agents as new chemical entities.

Язык: Английский

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Electrochemically Enable N-Sulfenylation/Phosphinylation of Sulfoximines via Oxidative Dehydrocoupling Reaction

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6106 - 6116

Опубликована: Апрель 18, 2024

An electrochemical oxidative cross-coupling strategy for the synthesis of N-sulfenylsulfoximines from sulfoximines and thiols was accomplished, giving diverse in moderate to good yields. Moreover, this can be extended construct N–P bond N-phosphinylated sulfoximines. With electrons as reagents, dehydrogenation reaction proceeds smoothly absence traditional redox reagents.

Язык: Английский

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Accelerating Electrochemical Synthesis through Automated Flow: Efficient Synthesis of Chalcogenophosphites

Synlett, Год журнала: 2020, Номер 31(19), С. 1894 - 1898

Опубликована: Июнь 16, 2020

Integrated electrochemical reactors in automated flow systems have been utilised for chalcogenophosphite formations. Multiple reactions can be performed using a programmed sequence fully autonomous way. Differently functionalised chalcogenophosphites efficiently synthesised short reaction times.

Язык: Английский

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Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water

European Journal of Organic Chemistry, Год журнала: 2021, Номер 2021(26), С. 3743 - 3747

Опубликована: Июнь 25, 2021

Abstract An efficient and chemoselective synthesis of sulfoxides through the electrooxidation sulfides has been well developed. This protocol takes advantage electricity as terminal oxidant molecular oxygen water atom sources. A variety structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled‐up reactions at 6–20 mmol show good practicability application potential this methodology. possible free radical mechanism proposed rationalize reaction procedure.

Язык: Английский

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Electrochemical oxidative dehydrogenation of hydrosilanes to generate silyl radicals: an efficient method for the construction of Si–O/Si–Si bonds utilizing a recyclable ionic liquid catalyst

Green Chemistry, Год журнала: 2024, Номер 26(19), С. 10189 - 10195

Опубликована: Янв. 1, 2024

A highly efficient and sustainable approach was developed for the construction of Si–O/Si–Si bonds, through electrochemical oxidative dehydrogenation hydrosilanes with O -nucleophiles or self-condensation hydrosilanes.

Язык: Английский

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Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(2), С. 464 - 469

Опубликована: Дек. 5, 2020

Abstract The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging task. We report herein on the direct regiodivergent N1/C2 phosphorylation free indole derivatives. Cyclic voltammograms EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate active species, diverse collection N1 C2 products could be obtained in moderate high yields under exogenous‐oxidant‐free metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found compatible with various alkylamines. magnified image

Язык: Английский

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