Collaborative Reduction-Induced Nickel-Catalytic Selective C–S Coupling of Aryl Di/Trithiosulfonates with Aryl Halides DOI
Lulu Liu, Jiaqi Hou, Yingying Ma

et al.

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

Published: Dec. 25, 2024

Metal-catalytic conversion of polysulfide reagents is a major challenge in organic synthesis due to its challenging activation modes multiple S–S bonds. The utilization aryl di- and trithiosulfonates nickel-catalyzed reductive coupling with halides has been unexplored. Herein, we unprecedentedly describe PPh3 Zn-collaborative reduction-induced nickel-catalytic selective C–S di/trithiosulfonates access sulfides over common disulfides or trisulfides. Diverse mechanistic studies indicate that the key design such reaction could be attributed employment MgCl2, which collaborate Zn for improved reduction potential enables cleavage PhSO2(S)naryl (n = 2, 3) electrophilic sulfur species sulfuration controllable fashion.

Language: Английский

A versatile entry to unnatural, disulfide-linked amino acids and peptides through the disulfuration of azlactones DOI Creative Commons

M Iwata,

Yuzuki Takami,

Hayato Asanuma

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An efficient method for preparing SS -linked amino acid/peptide derivatives has been developed via a base-catalyzed disulfuration reaction of azlactones, followed by ring-opening functionalization.

Language: Английский

Citations

1
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
NHC-BH3-Mediated Reduction of Sulfonyl Hydrazides into Disulfides and Further Cross-Coupling with Chlorostibine and Bioactivities DOI
Wen‐Jun Zhou,

Liyuan Le,

Youwen Chen

et al.

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

Published: Feb. 17, 2025

This paper presents a novel NHC-BH3-promoted one-step synthesis of disulfides and stibine sulfides using odorless sulfonyl hydrazides. The protocol tolerates various functional groups as well heterocyclic compounds. Mechanistic studies show that NHC-BH3 plays two roles: (1) reducing hydrazides into (2) promoting the cross-coupling chlorostibine with disulfides. synthesized also exhibit satisfactory anticancer activity against 4T1 MDA-MB-231 cancerous cells.

Language: Английский

Citations

0
Synthesis of Unsymmetrical Disulfides via Photocatalytic Hydrodisulfuration DOI

Qi-Rui Dong,

Yisen Wang, Juan Zhang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18237 - 18246

Published: Nov. 26, 2024

Language: Английский

Citations

2
Iron-Catalyzed Markovnikov-Selective Radical Hydrochalcogenation of Unactivated Alkenes DOI
Jiayi Li, Xia Liu, Zhaohui Liu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 14 - 22

Published: Dec. 12, 2024

A Markovnikov-selective radical hydrochalcogenation reaction of unactivated alkenes via iron-catalyzed hydrogen atom transfer was reported. Using N-(arylsulfenyl)arenesulfonamide, PhSO2SCD3, S-alkyl thiosulfonate, dithiosulfonate and Ebselen derivatives as versatile radicalophiles, a wide range unsymmetrical alkyl-aryl, dialkyl SCD3 (D > 99%) containing sulfides, disulfides, well organoselenides have been collectively synthesized under mild conditions. As powerful alternative to the classical thiol–ene reaction, this protocol features exclusive Markovnikov selectivity, good functional group tolerance broad substrate scope. number probe experiments suggest proceeds through pathway. The synthetic utility transformation also demonstrated late-stage modifications diverse natural products bioactive molecules.

Language: Английский

Citations

2
Recent Advances in Visible Light Photocatalytic and Transition Metal-Catalyzed Synthesis of Disulfide Compounds DOI
Jia‐Lin Tu

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

Published: Jan. 1, 2024

Reviewing photocatalytic and metal-catalyzed disulfide synthesis, 2021–2024, emphasizes efficiency, selectivity, sustainability for drug material science.

Language: Английский

Citations

0
Collaborative Reduction-Induced Nickel-Catalytic Selective C–S Coupling of Aryl Di/Trithiosulfonates with Aryl Halides DOI
Lulu Liu, Jiaqi Hou, Yingying Ma

et al.

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

Published: Dec. 25, 2024

Metal-catalytic conversion of polysulfide reagents is a major challenge in organic synthesis due to its challenging activation modes multiple S–S bonds. The utilization aryl di- and trithiosulfonates nickel-catalyzed reductive coupling with halides has been unexplored. Herein, we unprecedentedly describe PPh3 Zn-collaborative reduction-induced nickel-catalytic selective C–S di/trithiosulfonates access sulfides over common disulfides or trisulfides. Diverse mechanistic studies indicate that the key design such reaction could be attributed employment MgCl2, which collaborate Zn for improved reduction potential enables cleavage PhSO2(S)naryl (n = 2, 3) electrophilic sulfur species sulfuration controllable fashion.

Language: Английский

Citations

0