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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Synthesis of medium-sized benzo[b]azocines and benzo[b]azonines by photoinduced 8-/9-endo sulfonyl-cyclization

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(8), P. 2309 - 2316

Published: July 24, 2023

Language: Английский

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Visible-Light-Promoted Selective Sulfonylation and Selenylation of Dienes to Access Sulfonyl-/Seleno-benzazepine Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4208 - 4213

Published: May 30, 2023

A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed. This technology provides mild access to a wide range sulfonyl benzo[b]azepinones seleno-benzo[b]azepines. Preliminary mechanistic studies suggest that the involves radical engaged cascade process, is accomplished through sequential oxidation/electrophilic cyclization process. The large-scale operation late-stage modification experiment reveal promising utility this protocol.

Language: Английский

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Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7485 - 7507

Published: Jan. 1, 2023

The recent advances on the electrochemical selenofunctionalization of unsaturated C–C bonds were comprehensively summarized in this review.

Language: Английский

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Cascade Radical Trifluoromethylthiolation/Cyclization of Dienes To Access SCF₃-Containing Medium-Sized Heterocycles

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4598 - 4602

Published: June 12, 2023

A novel radical cascade trifluoromethylthiolation/cyclization of dienes (N-alkyl-2-(1-phenylvinyl)aniline derivatives) with AgSCF3 has been developed. This approach provides simple and efficient access to a wide range SCF3-containing medium-sized rings (7/8/9-membered heterocycles). Preliminary mechanistic studies suggest that the reaction is realized through silver-assisted cyclization process. The large-scale experiment modification product reveal promising utility this protocol.

Language: Английский

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Versatile electrooxidative amino- and oxyselenation of alkenes

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3925 - 3930

Published: Jan. 1, 2023

We herein describe a methodology for the production of organoselenium compounds by electrocatalytic difunctionalisation alkenes.

Language: Английский

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Photo- or Electrochemical Cyclization of Dienes with Diselenides to Access Seleno-Benzo[b]azepines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7245 - 7255

Published: May 23, 2023

A cascade selenylation/cyclization of dienes with diselenides has been realized under visible-light irradiation or electrolysis conditions. Employing O2 electricity as a "green" oxidant, this protocol provides green and efficient method for an array biologically important seleno-benzo[b]azepine derivatives in moderate to good yields. The direct sunlight gram-scale reaction render the approach practical attractive.

Language: Английский

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Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

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Chemoselective electrochemical seleno-cyclization of dienes to medium-sized benzo[b]azocines

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109058 - 109058

Published: Sept. 10, 2023

Language: Английский

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N-Fluorobenzenesulfonimide-Mediated Intermolecular Carboselenenylation of Olefins with Aromatics and Diselenides

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14609 - 14622

Published: Oct. 25, 2022

Intermolecular carboselenenylation of easily accessible alkenes by utilizing diselenides and N-fluorobenzenesulfonimide (NFSI) under metal-free mild conditions is reported. Preliminary mechanistic studies indicate that the oxidation diselenide NFSI through a single-electron-transfer process produces an active selenenyl cationic radical species initiates intermolecular olefins, forming key Se-C C-C bonds. Under optimized conditions, broad spectrum functionally structurally diverse selenoether derivatives with promising yields accessed very high functional group tolerance.

Language: Английский

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