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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P^III/P^V═O Redox Catalysis Mediated Thioesterification of Carboxylic Acids with Disulfides under Air Conditions

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

Published: Jan. 12, 2025

An efficient organophosphorus-catalyzed thiocarbonylation reaction of disulfides with carboxylic acids under air conditions was described. Various functional groups on and can be tolerated the present conditions, affording thioesters in good to excellent yields. This method exhibited chemoselectivity applied for late-stage functionalization drug molecules containing a acid group.

Language: Английский

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Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes

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

Published: April 22, 2025

Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series trifluoromethyl sulfonates were synthesized via visible-light-induced radical reaction sodium sulfinates and to obtain protons from solvent. dithiosulfonated derivatives bifunctionalization dithiosulfonates.This strategy has advantages mild conditions, good substrate universality high yield up 99% yield.

Language: Английский

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P^III/P^V-Catalyzed Beckmann Reaction and Sequential [2,3]-Sigmatropic Rearrangement to Construct 2-Amidopyridines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3536 - 3540

Published: April 24, 2024

An organophosphorus catalytic method for the synthesis of substituted 2-amidopyridines is reported. The employs a small-ring organophosphorus-based catalyst and hydrosilane reductant to drive conversion ketoximes pyridine-N-oxides into through sequential Beckmann rearrangement followed by [2,3]-sigmatropic rearrangement. readily available could be activated nitrilium ions in PIII/PV redox catalysis efficiently participate domino reaction pyridine-N-oxides, thus providing various moderate excellent yields. This presented strategy features functional group tolerance broad substrate scope.

Language: Английский

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