Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(52)

Published: June 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.

Language: Английский

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Highly Stereoselective Synthesis of Tetrasubstituted Vinyl Selenides via Rhodium-Catalyzed [1,4]-Acyl Migration of Selenoesters and Diazo Compounds

Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2175 - 2180

Published: March 14, 2022

Herein, we disclose a highly stereoselective Rh(II)-catalyzed 1,4-acyl rearrangement of selenium esters and α-diazo carbonyl compounds, which provides an efficient method for synthesizing tetrasubstituted vinyl selenides. Furthermore, this reaction also offers synthetic tool medium large ring compounds.

Language: Английский

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Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7216 - 7224

Published: May 2, 2024

An organoselenium-catalyzed C2,3-diarylation of unprotected N–H indoles with electron-rich aromatics has been developed. This one-pot multicomponent tandem cross-dehydrogenation coupling reaction allows for the incorporation two different aromatic groups to indoles. More importantly, this approach offers significant advantages, including a high atom and step economy, eliminating need prepreparation substrates, streamlining synthetic process enhancing its practicality. Overall, presents an efficient versatile strategy functionalization indole derivatives.

Language: Английский

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Porous Organic Polymers Catalyzed by Selenides: Recognition of Selenide-Induced Oxidative Coupling and Promoting Synergistic Hydrogenation of Nitroarenes with Pd Loading

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

Published: April 24, 2025

Language: Английский

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Organoselenium Compounds in Catalysis

Synthesis, Journal Year: 2023, Volume and Issue: 56(15), P. 2295 - 2315

Published: Oct. 24, 2023

Abstract In this article we have focused on the use of selenium in catalysis along with proposed reaction mechanisms. With increasing interest chemistry, highlighted most significant features subject, mainly last years. Selenium-containing catalysts a key role many transformations; for example, oxidation reactions that are performed under very mild and controlled conditions. addition, utilizing weak selenium–oxygen bonding interaction has proved to be useful as catalytic approach specific transformations. The cycles each appropriate transformation fully reviewed. 1 Introduction 2 Use Selenium Catalysis: Perspectives 2.1 Directing Group: Preparation Organoselenium Compounds via C–H Borylation 2.2 Multicomponent Reactions Employing Catalyst 2.3 Selenium-π-Acid Catalysts 2.4 Electrochemical Selenium-Catalyzed 2.5 Stereoselective Synthesis 2.6 Transition-Metal Containing Selenium-Based Ligands 2.6.1 Selenium-Ligated Palladium(II) Complexes Heck Reaction 2.6.2 Pincer Allylation Aldehydes Closely Related Functional Groups 2.6.3 Employed Buchwald-Type C–N Coupling 2.6.4 Suzuki–Miyaura 2.7 Catalysis Michael-Type 2.8 Catalytic Cycle Glutathione Peroxidase 2.9 Epoxidation 2.10 Dihydroxylation 2.11 Oxidation 2.12 Bromolactonization 2.13 Alkenes from Vicinal Diols 2.14 α-Selanyl Enals Propargylic Alcohols 2.15 Miscellanea 3 Concluding Remarks

Language: Английский

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O₂-Mediated Te(II)-Redox Catalysis for the Cross-Dehydrogenative Coupling of Indoles

JACS Au, Journal Year: 2022, Volume and Issue: 2(6), P. 1318 - 1323

Published: June 16, 2022

Very few elements in the periodic system can catalytically activate O2, such as context of cross-dehydrogenative couplings. The development O2-activating catalysts is essential to enable new and sustainable reactivity concepts emerge, because these also often feature specific activating interactions with target substrates. In this context, unprecedented Te(II)/Te(III) catalyzed dehydrogenative C3-C2 dimerization indoles described herein. fact that O2 be directly utilized a terminal oxidant reaction, well absence any background without redox-active Te catalyst, constitute very important milestones for fields couplings tellurium catalysis.

Language: Английский

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A Tunable Cascade Reaction of Ureidomalonates and Alkenyl Azlactones for the Divergent Synthesis of Hydantoins with Distinct Functional Groups

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3365 - 3382

Published: Feb. 16, 2024

A tunable cascade reaction of ureidomalonates and alkenyl azlactones was disclosed, which gave rise to the construction N-aroyl α-amino acid ester imide-functionalized hydantoins in moderate good yields with excellent diastereoselectivities. The pathway precisely manipulated by organocatalysis phase-transfer/sunlight relay catalysis, respectively, realize divergent synthesis. successful gram-scale preparation representative products exhibited application potential this protocol. Mechanistic studies indicated that exchange phase transfer ethoxy anion played a key role altering pathway, sunlight might accelerate oxidation process at late stage triggered phase-transfer catalysis.

Language: Английский

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Copper(I)-Catalyzed Three-Component Selenosulfonation of Maleimides with Sulfonyl Hydrazides and Diselenides via Radical Relay

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15661 - 15669

Published: Nov. 1, 2022

By employing Cu(CH3CN)4PF6 as the catalyst and tert-butyl hydroperoxide oxidant, we realized a three-component radical selenosulfonation of substituted maleimides, sulfonyl hydrazides, diphenyl diselenides, providing series 3,4-selenosulfonylated succinimides in moderate to good yields. This reaction features broad substrate scopes, high functional-group tolerability, feasibility gram-scale synthesis, enabling one-step construction C–SO2 C–Se bonds under mild conditions. Preliminary mechanistic studies support free-radical-induced pathway.

Language: Английский

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A rhodium-catalyzed ylide formation/Smiles rearrangement reaction of chalcogenide ether and triazoles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(9), P. 2198 - 2203

Published: Jan. 1, 2023

A Rh( ii )-catalyzed highly stereoselective chalcogenide ylide formation/Smiles rearrangement reaction of diaryl thioether/selenoethers and triazoles was successfully developed.

Language: Английский

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Intermolecular Aza-Wacker Coupling of Alkenes with Azoles by Photo-Aerobic Selenium-π-Acid Multicatalysis

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9586 - 9593

Published: June 11, 2024

Herein, the intermolecular, photoaerobic aza-Wacker coupling of azoles with alkenes by means dual and ternary selenium-π-acid multicatalysis is presented. The title method permits an expedited avenue toward a broad scope N-allylated representative azinones under mild conditions functional group tolerance, as showcased in more than 60 examples including late-stage drug derivatizations. From regiochemical perspective, protocol complementary to cognate photoredox catalytic olefin aminations, they typically proceed through either allylic hydrogen atom abstraction or single electron oxidation alkene substrate. These methods predominantly result C–N bond formations at periphery less substituted position former π-bond (i.e., anti-Markovnikov selectivity). current process, however, operates radical-polar crossover mechanism, which solely affects selenium catalyst, thus allowing be converted strictly ionic two-electron transfer regime Markovnikov control. In addition, it shown that corresponding N-vinyl can also accessed sequential one-pot treatment base, emphasizing exquisite utility this method.

Language: Английский

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