Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones DOI

Xiaoqing Wen,

Mengxin Li, Xiaoyan Peng

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

A simple and high-yielding strategy to produce a variety of β-keto sulfides using asymmetrical symmetrical thiosulfonates with ketones under mild conditions is reported. It was found that the various substituted compounds, both electron-withdrawing electron-donating substituents, afforded wide range thiosulfones (α-thioaryl-β-keto sulfones) in moderate high yields. The transformations were reliable at gram-scale, thus illustrating their efficiency practicality. plausible mechanism for protocol also proposed.

Language: Английский

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

Radical 1,3-Hydrosulfonylation of Vinyldiazo Compounds with Sulfinyl Sulfones DOI
Tian Jing, Yuan‐Li Ding,

Wanting Fu

et al.

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

Published: Feb. 4, 2025

Sulfinyl sulfones, as high-valence sulfurization reagents, are widely used to assemble sulfur sources on carbon skeletons, such one-, two-, and four-carbon synthons, access organosulfur compounds. However, their reaction with three-carbon synthons has remained a mystery until now. We report here radical 1,3-hydrosulfonylation of vinyldiazo compounds sulfinyl sulfones. This not only represents the first example sulfones but also opens up application in monofunctionalization.

Language: Английский

Citations

0

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

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

Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones DOI

Xiaoqing Wen,

Mengxin Li, Xiaoyan Peng

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

A simple and high-yielding strategy to produce a variety of β-keto sulfides using asymmetrical symmetrical thiosulfonates with ketones under mild conditions is reported. It was found that the various substituted compounds, both electron-withdrawing electron-donating substituents, afforded wide range thiosulfones (α-thioaryl-β-keto sulfones) in moderate high yields. The transformations were reliable at gram-scale, thus illustrating their efficiency practicality. plausible mechanism for protocol also proposed.

Language: Английский

Citations

0