Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Chemistry - A European Journal, Год журнала: 2023, Номер 29(52)

Опубликована: Июнь 28, 2023

Abstract Selenium, originally described as a toxin, turns out to be crucial trace element for life that appears selenocysteine and its dimer, selenocystine. From the point of view drug developments, selenium‐containing drugs are isosteres sulfur oxygen with advantage presence selenium atom confers antioxidant properties high lipophilicity, which would increase cell membrane permeation leading better oral bioavailability. In this article, we have focused on relevant features atom, above all, corresponding synthetic approaches access variety organoselenium molecules along proposed reaction mechanisms. The preparation biological selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, other compounds will treated. We attempted condense most important aspects interesting examples chemistry into single article.

Язык: Английский

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2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 6798 - 6812

Опубликована: Апрель 25, 2024

We have demonstrated N-substituted 2-pyridones as an N,O-directing group for selective C(sp2)-H-activated thiolation, selenylation, and sulfonamidation of ortho C–H bonds benzamides. This method utilizes a cost-effective Cu(II)-salt catalyst instead precious metal catalysts, achieving high yields, including gram-scale synthesis excellent functional tolerance. applied this protocol to access 30 different compounds with demonstrating thiolation fluorine-substituted benzamides well. Density theory (DFT) calculations support the mechanism, acetate-supported concerted metalation deprotonation (CMD) steps unique role dimethyl sulfoxide (DMSO) solvent. The facile pharmaceutically important sulfonamides other highlights method's potential in chemistry medicinal chemistry.

Язык: Английский

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Ruthenium(II)-Catalyzed C–H Activation/Annulation of 5-Phenyl-pyrroline-2-carboxylates with Alkynes: Synthesis of 2,3-Diphenylspiro-[indene-1,2′pyrrolidine]carboxylate Derivatives

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 8, 2025

While saturated nitrogen heterocycles are privileged scaffolds, their streamlined catalytic synthesis with unsymmetrical substitution patterns remains a daunting challenge. Herein, we report the ruthenium(II)-catalyzed of spiro[indene-proline] derivatives via C-H activation/annulation 5-phenyl-pyrroline-2-carboxylates alkynes. The protocol utilized imine coordination, resulting in high reaction yields wide range functional group tolerance, scalability, and scaffold diversity. This annulation was successful even various biologically active pharmacophores. featured reversible metalation step suggested possibility base-assisted internal electrophilic pathway.

Язык: Английский

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Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation

Organic Letters, Год журнала: 2022, Номер 24(48), С. 8729 - 8734

Опубликована: Ноя. 29, 2022

A copper-catalyzed protocol furnishing N-arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, N-Ar-7-azaindoles. Sulfoximines based on medicinally relevant (phenothiazine, dibenzothiophene, thioxanthenone) also well tolerated. Detailed mechanistic studies indicate that the deprotometalation protodemetalation step is reversible step.

Язык: Английский

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Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(9), С. 985 - 989

Опубликована: Дек. 26, 2023

Comprehensive Summary A Ru(II)‐catalyzed ortho allylation reaction of N ‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This is an effective pathway for synthesizing 7‐azaindole derivatives a wide scope substrates and high yields. In addition, the method can be extended to other heterocyclic compounds several carbonates, highlighting practicality this strategy synthesis.

Язык: Английский

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Copper‐Promoted Oxidative Amide‐Assisted Radical Selenylation of Anilides and N‐Arylsulfonamides with Diselenides

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(5)

Опубликована: Март 21, 2024

Abstract A direct selenylation of N ‐arylsulfonamides and anilides using environmentally friendly readily available copper promoted assisted by amide is presented. This method provided convenient access for various reactions, demonstrating a wide range substrates strong tolerance to functional groups. According the selection reaction substrates, products can be isolated obtain regioselectivity ortho ‐, para or unprecedented , ‐diselenylation products. Such transformation was elucidated proposed copper‐promoted amide‐assisted radical mechanism.

Язык: Английский

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I₂/DMSO Mediated Direct Selenylation of Uracils with Diorganoyl Diselenides – A Simple Protocol to Access 5‐Selanyl‐Uracils

ChemistrySelect, Год журнала: 2024, Номер 9(21)

Опубликована: Июнь 3, 2024

Abstract This study demonstrates a direct and regioselective selenylation protocol of unprotected uracils with diorganoyl diselenides using equivalent amount DMSO as oxidant minimum solvent, under catalysis by molecular iodine. methodology tolerates broad scope functional groups to provide several 5‐organoseleno‐substituted uracil derivatives in good excellent yields.

Язык: Английский

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Directing Group Guided Site‐Selective Alkylation of Indoles by Epoxides: Synthesis of β‐Indolylethyl Alcohol Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4416 - 4421

Опубликована: Авг. 7, 2024

Abstract A Palladium catalyzed C4‐ alkylation of indoles using epoxide as an alkylating agent and pivaloyl a weak chelating group has been demonstrated. variety substituted epoxides furnished the desired β‐indolylethyl alcohols in 38%–87% yields. Control experiments indicate that C−H cleavage step is irreversible. The resultant hydroxyl converted to various functional groups demonstrate synthetic utility this protocol.

Язык: Английский

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Regioselective C–H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(14), С. 2910 - 2916

Опубликована: Янв. 1, 2023

The reactions of direct Csp 2 –H chalcogenylation and halogenation N -arylpyrrolidone under the action PIFA without a directing group metal-free conditions were reported in this paper.

Язык: Английский

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Palladium-Catalyzed C(sp³)–H Biarylation of 8-Methyl Quinolines with Cyclic Diaryliodonium Salts to Access Functionalized Biaryls and Fluorene Derivatives

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 13744 - 13749

Опубликована: Окт. 5, 2022

Herein, we have developed the cyclic diaryliodonium salts as biarylating agents in C(sp3)–H functionalization using 8-methyl quinoline intrinsic directing group. The oxidant-free reaction produces a vast array of biarylated products with iodo functionality that can be further functionalized. Additionally, intramolecular stepwise manner under palladium-catalyzed conditions produced fluorene derivatives excellent yields.

Язык: Английский

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