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

Direct Cross-Couplings of Aryl Nonaflates with Aryl Bromides under Nickel Catalysis DOI
Hao Xu,

Jia-Wen Jing,

Yubing Chen

et al.

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

Published: Jan. 30, 2025

The direct cross-couplings of aryl nonaflates with bromides could be successfully accomplished by utilizing nickel as the catalyst, magnesium metal mediator, and lithium chloride additive. reactions proceeded efficiently in THF at room temperature to produce desired biaryls moderate good yields, showing both a reasonable substrate scope functional group tolerance. Additionally, an equally performance realized when reaction was subjected scale-up synthesis. Preliminary study suggested that presumably proceeds through situ formation arylmagnesium reagent key intermediate.

Language: Английский

Citations

1
Zn-promoted Sandmeyer-type reductive chalcogenation of (hetero)aryl diazonium salts DOI

Qiujin Fan,

Yanchuang Zhao,

Junhong Wang

et al.

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

Published: Jan. 1, 2025

In this report, we describe a nickel-free, zinc-induced reductive coupling between (hetero)aryl diazonium salts and electrophilic chalcogen species under mild reaction conditions.

Language: Английский

Citations

0
Magnesium-Mediated Three-Component Reductive Cross-Couplings of Aryl Aldehydes, Aryl Bromides, and Aryl 2-Pyridyl Esters: An Efficient Synthesis of Diarylmethanol Esters DOI
Xiaowei Han,

Yuan-Shuai Wu,

Tie Wu

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134558 - 134558

Published: Feb. 1, 2025

Language: Английский

Citations

0
Synthesis of Polyfluorinated Biaryls via Palladium-Catalyzed Decarboxylative Cross-Coupling of Zinc Polyfluorobenzoates with Aryl Fluorosulfates DOI

Bo-Wen Yang,

Jun Xu, Jie Pan

et al.

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

Published: April 11, 2025

A palladium-catalyzed decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl fluorosulfates, which proceeded efficiently via C-O bond cleavage to afford the corresponding polyfluorinated biaryls in moderate-to-good yields, was developed. The reactions exhibited both good substrate scope and broad functional group compatibility, it could be scaled-up easily. synthetic simplicity practicability reaction further demonstrated by one-pot manipulation directly mixing polyfluorobenzoic acid Zn(OH)2 coexistence fluorosulfate a palladium catalyst one flask. Further studies showed that is more robust than other halides pseudohalides as arylating reagent, polyfluorobenzoate effective polyfluoroarylating agent their magnesium potassium counterparts.

Language: Английский

Citations

0
Iron-Mediated One-Pot Dehydroxylative Cross-Electrophile Coupling of Alcohol with Disulfide for Thioether Synthesis by Using TCT as a Hydroxyl-Activating Agent DOI
Mengke Xu, X. Zhang, Yongqing Xu

et al.

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

Published: May 8, 2025

An efficient dehydroxythiolation between alcohols and disulfides using the widely abundant cheapest iron as a reaction mediator was developed. The one-pot thiolation proceeded effectively via C-O bond activation with aid of cyanuric chloride (TCT) hydroxyl-activating agent to give corresponding thioethers in modest excellent yields, displaying both wide substrate scope (applicable benzyl alcohol, allyl primary alkyl alcohol) good functional group tolerance. In addition, diselenide also proven be an appropriate for protocol, could subjected scale-up synthesis. Preliminary mechanistic examination revealed that transiently formed TCT-derived ether A, which is generated situ TCT possibly serves pivotal intermediate cross-electrophile thioetherification.

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