Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 10096 - 10110

Опубликована: Июль 3, 2023

Herein we report a cascaded chalcogenation of aryl alkynoates or N-arylpropynamides using 9-mesityl-10-methylacridinium perchlorate as visible light photocatalyst to obtain selectively either 3-sulfenylated/selenylated coumarins spiro[4,5]trienones. In radical initiated process, the spiro-cyclization reaction was favored due presence -OMe -F substituent at para position group, which helped stabilize allylic intermediate formed during reaction. Otherwise, 6-endo-trig cyclization led coumarins. Overall, new C–S/C–Se, C–C, and C═O bonds were in single step. The Stern–Volmer quenching study, EPR experiments, ON-OFF trapping etc., understand radical-based mechanism.

Язык: Английский

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From Reactive Oxygen Species to Reactive Brominating Species: Fenton Chemistry for Oxidative Bromination

ACS Sustainable Chemistry & Engineering, Год журнала: 2021, Номер 9(17), С. 6118 - 6125

Опубликована: Апрель 16, 2021

Fenton chemistry (FeII + H2O2 → HO•/HOO• H2O) generates reactive oxygen species (ROS) that are used for treatment of wastewater and oxidation organic molecules play a key role in biological systems. This study shows can be generation brominating (RBS) under neutral conditions at room temperature. The situ RBS successfully three types oxidative bromination reactions. green nonacidic new method addresses the safety environmental challenges existing methods. Additionally, this Fenton–bromide system long-lasting problem many functional haloperoxidase mimics required strong acids bromide ion with hydrogen peroxide. mild generating will significantly benefit wide applications brominated compounds synthesis fine chemical pharmaceutical industries.

Язык: Английский

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Study on the Application of Photoelectric Technology in the Synthesis of Selenium-Containing Heterocycles

Chinese Journal of Organic Chemistry, Год журнала: 2021, Номер 41(12), С. 4588 - 4588

Опубликована: Янв. 1, 2021

Selenium-containing heterocycles are a kind of important organic molecules, which widely used in medicine, agrochemicals, materials and other fields.Therefore, the introduction selenium atom into molecules is great significance synthetic chemistry.Visible light electrochemical technology one green sustainable synthesis methods, has opened up broad application prospects fields bifunctionalization cyclization unsaturated bonds direct functionalization C-H bonds.In recent years, development novel reaction using photoelectric to drive selenization attracted much attention.Therefore, this paper describes electrochemical-driven visible-light-induced reactions selenium-containing heterocycles, discusses applicable scope mechanism some reactions.

Язык: Английский

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Research Advances in Electrochemical Synthesis of Spirocyclic Skeleton Compounds

Synthesis, Год журнала: 2023, Номер 55(18), С. 2873 - 2895

Опубликована: Янв. 24, 2023

Abstract Spirocyclic compounds have attracted the interest of synthetic chemists because their unique ring systems and utility in drug discovery. Many natural containing spirocyclic moieties skeleton are effective pharmaceuticals. For many redox processes, electroorganic synthesis is considered an environmentally friendly method, since use reagents with significant toxicity replaced by electric current, so amount waste often greatly reduced. Therefore, this review summarizes construction a via electrochemical strategies 2000. 1 Introduction 2 Electrochemically Mediated Synthesis Spirocyclopropanes 3 Spirooxindoles 4 Spirodienones 5 Other Heterospirocycles 6 Conclusion

Язык: Английский

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Electrochemical Synthesis of Organoselenium Compounds: A Graphical Review

SynOpen, Год журнала: 2023, Номер 07(04), С. 511 - 520

Опубликована: Окт. 1, 2023

Abstract Electrochemical synthesis, due to its environmentally benign, sustainable, and practical nature, has become an appealing powerful substitute for traditional methods oxidizing reducing organic compounds. Thus, numerous valuable changes have been established in the field of synthesis through utilization electrochemistry. Among these electrochemical transformations, formation C–Se bonds stands out as exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary progress utilizing strategies synthesizing organoselenium

Язык: Английский

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Electrochemical Oxidative Carbonylation of NH-Sulfoximines

Organic Letters, Год журнала: 2023, Номер 25(41), С. 7529 - 7534

Опубликована: Окт. 11, 2023

The electrochemical synthesis of N-aroylsulfoximines features the use tetra-n-butylammonium iodide (TBAI) as medium and a broad substrate scope, thus affording wide range N-aroylated sulfoximines in moderate to good yields. advantages this strategy are augmented by mild reaction conditions that external oxidant-free, ligand-free, easy scale up gram scale. Both control experiments mechanistic studies revealed whole process proceeded through palladium (II/IV/II) catalytic cycle.

Язык: Английский

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Copper(ii)-catalyzed oxidative ipso-annulation of N-arylpropiolamides and biaryl ynones with 1,3-diketones: construction of diketoalkyl spiro-trienones

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(34), С. 6879 - 6889

Опубликована: Янв. 1, 2022

An unprecedented copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, which enables the assembly diketoalkylated spiro[4.5]trienones involving oxidative dearomatization in presence ammonium persulfate [(NH4)2S2O8] as oxidant. This protocol was extended to biaryl ynones, efficiently affording spiro[5.5]trienones good yields. The significance diketoalkyl functionality illustrated by further transformation into 3-pyrazoyl spiro-trienone, a structurally unique motif.

Язык: Английский

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Selective Electrochemical Halogenation of Functionalized Quinolone

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 12958 - 12970

Опубликована: Авг. 24, 2023

This work describes an effective C3–H halogenation of quinoline-4(1H)-ones under electrochemical conditions, in which potassium halides serve as both halogenating agents and electrolytes. The protocol provides expedient access to different halogenated with unique regioselectivity, broad substrate scope, gram-scale synthesis employing convenient, environmentally friendly electrolysis, undivided cell. Mechanism studies have shown that halogen radicals can promote the activation N–H bonds quinolones.

Язык: Английский

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Electrochemical Post-Ugi Cyclization for the Synthesis of Highly Functionalized Spirolactams

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13977 - 13994

Опубликована: Сен. 11, 2023

The combination of the Ugi reaction and electro-organic synthesis can aid in creation novel heterocycles that have not been previously explored. In this study, a new strategy utilizing bis-amides from has developed, which produce C–S, C–Se, C–C═O functionalized five-membered spirolactams mediated by electricity under catalyst- metal-free conditions. Notably, approach be applied using microelectro-flow reactor (μ-EFR) for gram-scale synthesis. described synthesize complex azaspiro-fused tricyclic scaffolds with high diastereo- regioselectivity, highlighting its versatility potential.

Язык: Английский

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Seleno/Thio-functionalized ipso-Annulation of N-Propiolyl-2-arylbenzimidazole to Construct Azaspiro[5,5]undecatrienones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16485 - 16496

Опубликована: Ноя. 9, 2023

Till date, the ipso-cyclization of propiolamides is limited to provide azaspiro[4,5]decatrienones. Herein, we present first example ipso-carbocyclization, leading azaspiro[5,5]-undecatrienones from N-propiolyl-2-arylbenzimidazoles, involving both radical-based and electrophilic reactions. This report establishes an access a wide range chalcogenated (SCN/SCF3/SePh) benzimidazo-fused azaspiro[5,5]undecatrienones in good yields.

Язык: Английский

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