Recent Advances in Deoxygenative Thioether Synthesis Using Oxygenated Sulfur Surrogates

Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Abstract Thioethers (sulfides) play a crucial role in therapeutics, diagnostics, and functional materials. Traditionally, their synthesis involved the use of thiols or derivatives, which are associated with unpleasant odors potential health risks. Recently, significant research has focused on employing oxygenated sulfur compounds, such as sulfinates, sulfonyl oxyacids, sulfoxides, thiol surrogates for thioether synthesis. This review highlights recent advancements deoxygenative synthesis, categorizing them by reaction types, including cross-coupling reactions, C–H functionalization, hydro/halo/oxy-thiolation unsaturated hydrocarbons. We also discuss representative mechanisms to provide comprehensive understanding these innovative approaches. 1 Introduction 2 Cross-Coupling Reactions 3 Functionalization 4 Hydro/Halo/Oxy-thiolation Unsaturated Hydrocarbons 5 Conclusion

Language: Английский

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Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 25, 2025

p-CF3BnSeCF2Br was developed as a bromodifluoromethylselenonating reagent, which utilized by combining with mCPBA and Tf2O for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via selenolation/lactonization 2-alkynylbenzoates. The transformation postulated to proceed multicomponent reagents system-enabled sequence involving oxidation into its selenium sulfoxide, activation generated sulfoxide electrophilic p-CF3BnSeOCF2Br salt, 2-alkynylbenzoates reactive species isocoumarins.

Language: Английский

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Organic Base-Catalyzed Cascade Reaction of CF₃–Iminopropargylic Alcohols with Carboxylic Acids: an Approach to β-CF₃ β-Aminoenones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

A novel approach to the synthesis of β-CF3 β-aminoenones by organic amine base-catalyzed reaction CF3-iminopropargylic alcohols with carboxylic acids is reported. The advantages protocol are ease operation, available starting materials, and simple tertiary catalysts.

Language: Английский

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Synthesis of Multisubstituted Arylnitriles via Tf₂O-Mediated Benzannulation of Enaminones with Acylacetonitriles

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 3, 2025

A novel and efficient method for the synthesis of multisubstituted arylnitriles via Tf2O-mediated [3 + 2 1] benzannulation enaminones acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation aromatization. Additionally, trifluoromethanesulfonate 6 identified as crucial intermediate in this process.

Language: Английский

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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Language: Английский

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Iridium-catalyzed reduction of o-hydroxyl phenyl enaminones for the synthesis propiophenones and their application in 3-methyl chromone synthesis

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A method of reducing

Language: Английский

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