Iodine/TBHP‐Promoted Cross Coupling of N‐Hydroxy Aryl Sulfonamides and Disulfides to Synthesize Unsymmetrical Thiosulfonates DOI Open Access

Jayshree Solanke,

Rana Chatterjee,

Savita Gat

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(46)

Published: Dec. 1, 2024

Abstract An efficient and novel method has been developed for the synthesis of structurally diverse unsymmetrical thiosulfonates via oxidative coupling reactions N ‐hydroxy aryl sulfonamides disulfides. The iodine TBHP system enables transformations to afford a variety with good high yields. Furthermore, large‐scale practical application access sulfonamide have investigated. Notably, present protocol offers easily accessible materials, wide range substrates, radical pathways, metal‐free conditions.

Language: Английский

Chromium‐Catalyzed Reductive Cross‐Coupling to Construct C−SS Bonds from Unactivated Alkyl Electrophiles DOI

Chao‐Peng Zhang,

Tian‐Zhang Wang,

Kang Wu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(15)

Published: March 15, 2024

Abstract Low‐valent chromium catalysts are cheap and less toxic compared to other transition metal catalysts. Here in, we reported a ligand‐free chromium(III)‐catalyzed manganese reductive cross‐coupling of unactivated alkyl electrophiles, such as sulfonates chlorides, with trisulfide dioxides thiolation agents form carbon−sulfur bonds. The powerful method featured ample substrate scope wide functional group tolerance, constructing large number unsymmetrical disulfides under simple conditions.

Language: Английский

Citations

7
Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation DOI

Xuan-Bo Hu,

Yuwei Chen, Chenlong Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13601 - 13607

Published: Sept. 4, 2024

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired sulfides in good yields, exhibiting both broad substrate scope and functionality tolerance. In addition, reaction could be applied use selenosulfonate as an effective selenylation agent subjected scale-up synthesis.

Language: Английский

Citations

7
Synthesis of Thioethers via Nickel-Catalyzed Cross-Coupling of Aryl Halides with Ketene Dithioacetal DOI

Baolong Xu,

Shaowen Ling,

Shengping Zheng

et al.

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

Published: Feb. 9, 2025

Herein, we present a nickel-catalyzed C–S cross-coupling between aryl halides and ketene dithioacetals under "base-free" conditions without an exogenous ligand. By employing easily available as sulfide donors, this reaction affords broad range of unsymmetrical alkyl-aryl sulfides using odorous toxic thiols. The newly developed catalytic methodology features excellent functional group tolerance, wide substrate scope, diverse downstream synthesis. Preliminary mechanism investigations reveal that Ni(I)/Ni(III) cycle might be involved.

Language: Английский

Citations

1
Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates DOI Creative Commons
Yu Guo,

Guotao Lin,

Mengjie Zhang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Aug. 25, 2024

Due to the high reactivity and versatility of benzenesulfonothioates, significant advancements have been made in constructing C-S bonds. However, there are certain limitations synthesis S-thiosulfonates SS-thiosulfonates, especially when dealing with substantial steric hindrance, which poses a challenge. Herein, we present an innovative approach for assembling unsymmetric SS-thiosulfonates through integration dual copper/photoredox catalysis. Moreover, also realized one-pot strategy by directly using carboxylic acids as raw materials in-situ activation them access without further purification presynthesis NHPI esters. The envisaged utilization these reagents poised pioneer pathway fabricating versatile spectrum mono-, di-, polysulfide compounds. Furthermore, they introduce class potent sulfenylating reagents, empowering intricate unsymmetrical disulfides that were previously challenging access. conventional method synthesizing thioether compounds typically relies on thiol, disulfide, sulfinyl halide initial substances, suffering from strong odors, limited availability, issues. Here, authors catalysis

Language: Английский

Citations

6
Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides DOI
Peng‐Fei Huang,

Jia-Le Fu,

Zhi-Gang Quan

et al.

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

Published: March 12, 2025

Organoselenium compounds and quinolines are widely used in drugs materials. Herein, we report an electro-oxidative cyclization between isocyanides diselenides to effectively synthesize 2-organoselenyl a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series produced with up 82% yield, good functional group tolerance high atom efficiency under room temperature.

Language: Английский

Citations

0
One-Pot Stepwise Dechalcogenization of Trisulfides to Unsymmetrical Dialkyl Thioethers DOI

Jiuwen Xu,

Ying Chen, Weidong Rao

et al.

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

Published: April 17, 2025

The construction of C-S bonds has garnered significant interest due to the ubiquitous presence organosulfur compounds in natural products and bioactive molecules. Herein, we report a one-pot, stepwise desulfuration strategy employing trisulfides as precursors for synthesis unsymmetrical dialkylthioethers. Our study demonstrates that copper powder facilitates conversion into disulfides, which subsequently undergo nickel-catalyzed reductive coupling afford desired products. This approach provides practical, odorless, broadly applicable method

Language: Английский

Citations

0
Iron‐Mediated Desulfonylative Cross‐Electrophile Couplings of Heteroaryl Sulfones with Thiosulfonates for Efficient Synthesis of Heteroaryl Sulfides DOI
Yuan He, Jie Pan, Ying Yan

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 28, 2025

Comprehensive Summary A desulfonylative thiolation between heteroaryl sulfones and thiosulfonates for the efficient synthesis of sulfides was developed. The cross‐electrophile couplings proceeded effectively via old C–SO 2 bond cleavage new C–S formation in presence cheapest widely available iron powder as mediator under transition metal catalyst‐free conditions, leading to a wide array derived from benzo[ d ]thiazole, ]oxazole, thiazole, 1,3,4‐thiadiazole, 1 H ‐tetrazole modest excellent yields. In addition, reaction exhibited good functional group compatibility, protocol could also be applicable use selenosulfonate substrate subjected scale‐up with equal ease. Notably, unreacted readily recovered after by resorting attracting property magnetic stir bar iron.

Language: Английский

Citations

0
Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry DOI Creative Commons
Luana Bagnoli, Ornelio Rosati, Francesca Marini

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: April 25, 2024

Abstract A mini review focused on the chemistry of selenosulfones reported since 2019 is here presented. Initially, methods aimed to preparation such moiety are discussed. Successively 1,2‐, 1,3‐, 1,4‐ and 1,7‐addition reactions C−C single multiple bonds illustrated. The forth chapter focuses electrophilic aromatic substitutions. fifth deals with C−H functionalizations while sixth one shows aryl diazonium salts or its precursors. radical coupling redox active reagents, subject section seventh. Selenosulfones challenged in nucleophilic substitutions phosphorus‐containing compounds shown eight nine followed by conclusions perspectives section.

Language: Английский

Citations

2
Copper(0)-Catalyzed Reductive Coupling of Disulfurating Reagents and (Hetero)aryl/Alkyl Halides DOI
Wang Chen,

Jiuwen Xu,

Weidong Rao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

Herein, we reported a copper(0)-catalyzed reductive coupling of disulfurating reagents and (hetero)aryl/alkyl halides. Copper(0) can be directly inserted into tetrasulfide then undergoes with (hetero)aryl Iodides to construct disulfide. The method features the unprecedented use (tetrasulfides) in cross-coupling chemistry is convenient broad substrate scopes, even applicable different halogenated hydrocarbons. It worth noting that methodology practical late-stage modification bioactive scaffolds pharmaceuticals. In meantime, synthesis disulfides successfully achieved on gram scale, indicating approach highly valuable.

Language: Английский

Citations

1
Iodine/TBHP‐Promoted Cross Coupling of N‐Hydroxy Aryl Sulfonamides and Disulfides to Synthesize Unsymmetrical Thiosulfonates DOI Open Access

Jayshree Solanke,

Rana Chatterjee,

Savita Gat

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(46)

Published: Dec. 1, 2024

Abstract An efficient and novel method has been developed for the synthesis of structurally diverse unsymmetrical thiosulfonates via oxidative coupling reactions N ‐hydroxy aryl sulfonamides disulfides. The iodine TBHP system enables transformations to afford a variety with good high yields. Furthermore, large‐scale practical application access sulfonamide have investigated. Notably, present protocol offers easily accessible materials, wide range substrates, radical pathways, metal‐free conditions.

Language: Английский

Citations

0