Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 8062 - 8066

Published: Oct. 24, 2022

An efficient base, additive and metal-free synthetic methods for α-ketothioamide α-ketoamide derivatives from readily available sulfoxonium ylides have been described. Sulfoxonium with primary or secondary amines afforded α-ketothioamides in the presence of elemental sulfur, whereas α-ketoamides were produced when I2 TBHP present. The reaction proceeded well at room temperature generated corresponding molecules good to excellent yields. can be scaled-up tolerated by a range functional groups simple operational procedures.

Language: Английский

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Hydroxyl-Directed Ru(II)-Catalyzed Synthesis of Fused Dihydrofurans Using 1,4-Dioxane and Sulfoxonium Ylides as Annulating Agents

Organic Letters, Journal Year: 2023, Volume and Issue: 25(1), P. 215 - 219

Published: Jan. 3, 2023

An unprecedented annulation reaction is developed for the synthesis of dihydrofuran-fused compounds. In this Ru-catalyzed hydroxyl-group-directed reaction, easily affordable sulfoxonium ylides and 1,4-dioxane were used as annulating partners. This first example use a methylene source to construct heterocyclic scaffold. A wide range dihydrofuran0fused coumarins naphthalenes synthesized using three-component reaction.

Language: Английский

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Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5572 - 5585

Published: April 21, 2023

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling α-keto sulfoxonium ylides with diselenides. The versatility electrochemical manifold enabled selenylation ample scope broad functional group tolerance, as well setting stage for modification complex bioactive Detailed mechanistic studies revealed that key C-Se bond was constructed using n-Bu4NI an electrolyte catalyst electrosynthetic protocol. Finally, desired showed excellent antimicrobial activity against Candida albicans, which can be identified lead further exploration.

Language: Английский

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Synthesis of α-Carbonyl-α′-amide Sulfoxonium Ylides from Isocyanates with Complete Atom Economy

Organic Letters, Journal Year: 2023, Volume and Issue: 25(7), P. 1214 - 1217

Published: Feb. 9, 2023

An efficient catalyst- and additive-free facile synthesis of α-carbonyl-α′-amide sulfoxonium ylides from isocyanates β-ketosulfoxonium with complete atom economy has been described. The adorned various functional groups were well-tolerated afforded moderate to high yields the ylide derivatives. Finally, using large-scale reactions converting synthesized into other valuable compounds, we demonstrated practicality this synthetic method.

Language: Английский

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Photocatalytic synthesis of dual acylmethylation derivates of indole[2,1-a]isoquinolinones via tandem cyclization/C3 acyl methylation

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 580, P. 115058 - 115058

Published: April 15, 2025

Language: Английский

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Elemental Sulfur-Mediated Synthesis of Quinoxalines from Sulfoxonium Ylides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5329 - 5332

Published: July 7, 2023

A novel straightforward and catalyst-free approach for synthesizing quinoxaline derivatives from sulfoxonium ylides o-phenylenediamines mediated by elemental sulfur has been described. Due to the simple mild reaction conditions, decorated with different functional groups furnished moderate high yields of were well tolerated. Finally, large-scale reactions, synthesis pyrazines, some bioactive compounds are used illustrate potential utility developed approach.

Language: Английский

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α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(5), P. 879 - 909

Published: Dec. 6, 2022

Transition metal-catalyzed cross-coupling of sp2 C-H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction C-C and C-heteroatom in organic synthesis. Despite popularity as coupling partners activation, they pose serious safety stability issues due to potential exothermic reactions linked release N2 gas. However, compared compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used industrial scales, easier/safer prepare. Therefore, recent years have witnessed upsurge employing α-carbonyl alternative surrogate transition activation. Unlike contain inherent serve a partner well weak directing group. This review will summarize progress made both categories reactions.

Language: Английский

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Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(46), P. 8503 - 8508

Published: Nov. 11, 2022

Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular SY in presence a chiral diene up 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that re face olefin preferably attacks an iridium carbene intermediate asynchronous concerted step is independent geometry olefin.

Language: Английский

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Straightforward access to α-thiocyanoketones and thiazoles from sulfoxonium ylides

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(68), P. 10247 - 10250

Published: Jan. 1, 2023

Efficient, versatile, and metal-free strategies for synthesizing α-thiocyanoketones thiazoles from β-ketosulfoxonium ylides ammonium thiocyanate have been described. Due to its simplicity, benign reaction conditions, excellent chemoselectivity, high yield, this method represents a unique approach divergent synthesis. Finally, the potential value of developed methods is demonstrated via large-scale reactions synthesis Fanetizole, an anti-inflammatory drug.

Language: Английский

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Catalyst- and additive-free syntheses of rhodanine andS-alkyl dithiocarbamate derivatives from sulfoxonium ylides

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(11), P. 1509 - 1512

Published: Jan. 1, 2023

An efficient catalyst- and additive-free facile access to rhodanine S -alkyl dithiocarbamate derivatives via multi-component reaction of amines, CS 2 α-ester sulfoxonium ylides in methanol has been described.

Language: Английский

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