PotassiumO‐Ethyl Xanthate DOI
Radomir N. Saičić, Zorana Ferjančić

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2022, Volume and Issue: unknown, P. 1 - 19

Published: July 18, 2022

[140-89-6] C3H5KOS2 (MW 160.30) InChI = 1S/C3H6OS2.K/c1-2-4-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1 InChIKey JCBJVAJGLKENNC-UHFFFAOYSA-M (preparation of thiols, sulfides, and disulfides; heterocycle formation; reaction with alkyl halides leads to the formation xanthates which are versatile radical precursors; glycosidation; esterification) Alternate Name: potassium xanthate, xanthogenate, O-xanthogenate, carbonodithioic acid O-ethyl ester salt, S-potassium dithiocarbonate. Physical Data: mp 222 °C1; density 1.558.21.5 Solubility: very soluble in cold water; decomposes hot ethanol; insoluble ether. Form Supplied in: pale yellow solid. Preparative Methods: commercially available. Potassium ethyl xanthate its congeners can be prepared by corresponding alkoxide carbon disulfide.2,3 Methods purification commercial compound,4 as well for preparation extremely pure derivatives have been reported.5 Handling, Storage, Precaution: reasonably stable when stored a dark place, protected from air moisture.

Language: Английский

Recent Advances in Deoxygenative Thioether Synthesis Using Oxygenated Sulfur Surrogates DOI
Cong Ma, Long Yin Lam

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

Citations

1
Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates DOI
Qiao Sun, Yuan Xu,

Liu Yang

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: Feb. 29, 2024

Abstract In light of the important biological activities and widespread applications organic disulfides, dithiocarbamates, xanthates, thiocarbamates thiocarbonates, continual persuit efficient methods for their synthesis remains crucial. Traditionally, preparation such compounds heavily relied on intricate multi‐step syntheses use highly prefunctionalized starting materials. Over past two decades, direct sulfuration C−H bonds has evolved into a straightforward, atom‐ step‐economical method organosulfur compounds. This review aims to provide an up‐to‐date discussion disulfuration, dithiocarbamation, xanthylation, thiocarbamation thiocarbonation, with special focus describing scopes mechanistic aspects. Moreover, synthetic limitations some these methodologies, along key unsolved challenges be addressed in future are also discussed. The majority examples covered this accomplished via metal‐free, photochemical or electrochemical approaches, which alignment overraching objectives green sustainable chemistry. comprehensive consolidate recent advancements, providing valuable insights dynamic landscape strategies crucial classes

Language: Английский

Citations

4
Salt resistance study and molecular dynamics simulation of hydrophobic-association polymer with internal salt structure DOI
Quan Zhang, Jincheng Mao,

Yuemin Liao

et al.

Journal of Molecular Liquids, Journal Year: 2022, Volume and Issue: 367, P. 120520 - 120520

Published: Oct. 6, 2022

Language: Английский

Citations

10
Redox-active alkyl xanthate esters enable practical C–S cross-coupling by nickel catalysis DOI

Lanzhu Tai,

Li Chen,

Yuxuan Shi

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(10), P. 2505 - 2516

Published: Jan. 1, 2023

A new nickel catalysis strategy that harnesses readily accessible alkyl xanthate esters, while previously well-studied as radical precursors, herein ideal sulfenylating agents via an unprecedented C–S bond activation pattern.

Language: Английский

Citations

5
Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane DOI

Liubov I. Panferova,

Mikhail O. Zubkov, Mikhail D. Kosobokov

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(46), P. 8559 - 8563

Published: Nov. 9, 2022

The removal of the tetrafluoropyridinyl group tethered to a sulfur atom using complex N-heterocyclic carbene (NHC) with borane is described. reaction performed under blue light irradiation disulfide as radical initiator. selective cleavage S-Ar in preference weaker S-Alk bond achieved result aromatic substitution thiyl by NHC-stabilized boron-centered radical. Alkyl thiols, which are primary products dearylation, situ oxidized or alkylated, affording disulfides sulfides, respectively.

Language: Английский

Citations

9
Expedient Syntheses of Alkyl and Aryl Thioethers using Xanthates as Thiol-Free Reagents DOI Open Access

Jinli Nie,

Ziqing He,

Sijie Xie

et al.

Published: May 15, 2024

Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most methods for synthesizing alkyl thioethers employ foul-smelling thiols as starting materials or generate them by-products. Additionally, air-sensitive easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method is necessary. This paper reports simple, effective, green dialkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K thiol surrogate. transformation offers broad substrate scope good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated nucleophilic substitution halides transition-metal-free base-free conditions.

Language: Английский

Citations

1
KI/K2S2O8 Mediated Cascade C(sp3)−H/C(sp2)−H Thiolation for the Synthesis of Multi‐Substituted Thiazoles DOI
Lang Liu, Jun Zhang

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(17)

Published: April 14, 2022

Abstract Thiazole and carbonyl often act as core functional or regulative moieties in biological molecules well optical materials. Designing synthesis of carbonyl‐containing thiazoles are great importance for related fields, hence, a simple practical method was developed using commercially xanthates, benzylamine, readily available alkynones substrates. The reaction achieved one‐pot Michael addition cascade iodine mediated C−H thiolation under mild conditions. This features broad substrate scope with high yield. Remarkably, the obtained substituted bearing electronic‐donating substituents exhibit promising performance aggregation‐induced emission (AIE) have been successfully used imaging.

Language: Английский

Citations

3
A novel approach to obtain 3-amino-1-benzothiophene-2-carbonitriles DOI
Dmitry S. Ivanov,

Анатолий И. Соколов,

Alexander Yu. Smirnov

et al.

Chemistry of Heterocyclic Compounds, Journal Year: 2024, Volume and Issue: 60(1-2), P. 99 - 102

Published: Feb. 1, 2024

Language: Английский

Citations

0
Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents DOI Creative Commons

Jinli Nie,

Ziqing He,

Sijie Xie

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2485 - 2485

Published: May 24, 2024

Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most methods for synthesis alkyl thioethers employ foul-smelling thiols as starting materials or generate them by-products. Additionally, air-sensitive easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method synthesizing is necessary. This paper reports simple, effective, green dialkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K thiol surrogate. transformation offers broad substrate scope good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated nucleophilic substitution halides transition-metal-free base-free conditions.

Language: Английский

Citations

0
PotassiumO‐Ethyl Xanthate DOI
Radomir N. Saičić, Zorana Ferjančić

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2022, Volume and Issue: unknown, P. 1 - 19

Published: July 18, 2022

[140-89-6] C3H5KOS2 (MW 160.30) InChI = 1S/C3H6OS2.K/c1-2-4-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1 InChIKey JCBJVAJGLKENNC-UHFFFAOYSA-M (preparation of thiols, sulfides, and disulfides; heterocycle formation; reaction with alkyl halides leads to the formation xanthates which are versatile radical precursors; glycosidation; esterification) Alternate Name: potassium xanthate, xanthogenate, O-xanthogenate, carbonodithioic acid O-ethyl ester salt, S-potassium dithiocarbonate. Physical Data: mp 222 °C1; density 1.558.21.5 Solubility: very soluble in cold water; decomposes hot ethanol; insoluble ether. Form Supplied in: pale yellow solid. Preparative Methods: commercially available. Potassium ethyl xanthate its congeners can be prepared by corresponding alkoxide carbon disulfide.2,3 Methods purification commercial compound,4 as well for preparation extremely pure derivatives have been reported.5 Handling, Storage, Precaution: reasonably stable when stored a dark place, protected from air moisture.

Language: Английский

Citations

0