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

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

Citations

15
Generation of perthiyl radicals for the synthesis of unsymmetric disulfides DOI Creative Commons

Fei Zhou,

X. He, Mi Zhou

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 2, 2025

Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside a single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously. Here, authors novel transition-metalfree

Language: Английский

Citations

0
Photocatalytic selective disulfuration of aryl aldehydes and alkenyl aldehydes with dithiosulfonate as bifunctional disulfur reagent and hydrogen atom accepter DOI

Jingchao Jiao,

Juan Xu, Jingru Li

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We developed a photocatalytic method for the selective disulfuration of aryl aldehydes and alkenyl using bifunctional dithiosulfonate (ArSO 2 -SSR), enabling synthesis benzoyl disulfides chroman-4-ones with disulfide moieties.

Language: Английский

Citations

0
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
Boosting porphyrin photocatalysis in thiophenol cross-coupling via supramolecular host-guest engineering DOI

Guang-Lu Li,

Xuan‐Zong Yang,

Rongxin Zhu

et al.

Dyes and Pigments, Journal Year: 2025, Volume and Issue: unknown, P. 112860 - 112860

Published: April 1, 2025

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

1
New Approach to Perthiyl Radicals for the Synthesis of Unsymmetric Disulfides DOI
Zhong Lian,

Fei Zhou,

X. He

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 9, 2024

Abstract Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report a novel transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks inaugural use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process were verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously.

Language: Английский

Citations

0
Chloride Induced S-C bond Selective Cleavage of Disulfides to Access Unsymmetrical β-Fluorodisulfides DOI
Tengfei Niu, Jiayuan Zhang, Yunpeng He

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This work describes a novel chloride anion induced radical-triggered S–C bond selective cleavage of disulfides to access unsymmetrical β-fluorodisulfides by disulfidefluorination alkenes.

Language: Английский

Citations

0
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