Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates DOI
Xiaowei Han, Yuan He,

Chao Gui

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13661 - 13668

Published: Sept. 9, 2024

Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides the aid of magnesium as a reducing metal in absence transition-metal catalyst, leading to unsymmetrical diaryl ketones modest good yields wide functionality compatibility. In addition, reaction be easily scaled up and applied late-stage modification biologically active molecules. Preliminary mechanistic study showed that coupling presumably proceeds through situ formation arylmagnesium reagents key intermediates.

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
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

5
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
Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates DOI
Xiaowei Han, Yuan He,

Chao Gui

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13661 - 13668

Published: Sept. 9, 2024

Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides the aid of magnesium as a reducing metal in absence transition-metal catalyst, leading to unsymmetrical diaryl ketones modest good yields wide functionality compatibility. In addition, reaction be easily scaled up and applied late-stage modification biologically active molecules. Preliminary mechanistic study showed that coupling presumably proceeds through situ formation arylmagnesium reagents key intermediates.

Language: Английский

Citations

3