Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides DOI Creative Commons
Haifeng Yu, Wanting Zhang, Xuejing Cui

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2225 - 2233

Published: Sept. 3, 2024

An eco-friendly selective hydrolysis of chain α-oxo ketene N , S -acetals in water for the switchable synthesis β-keto thioesters and amides is reported. In refluxing water, reactions presence 1.0 equiv dodecylbenzenesulfonic acid effectively afforded excellent yield, while were successfully obtained yield when carried out 3.0 NaOH. The green approach to avoids use harmful organic solvents, thiols thiolacetates as well amines, which could result serious environmental safety issues.

Language: Английский

Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides DOI
Wei‐Cheng Yuan, Xiaohui Fu, Yanping Zhang

et al.

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

Published: Feb. 10, 2025

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.

Language: Английский

Citations

0
Copper-catalyzed sulfonylation of alkenes with CH3SSO3Na DOI Creative Commons
Xiaoli Chen, Ge Wu

BMC Chemistry, Journal Year: 2025, Volume and Issue: 19(1)

Published: Feb. 22, 2025

A successful methodology for the copper-catalyzed dehydrogenated methylsulfonylation of alkenes utilizing CH3SSO3Na in conjunction with hypervalent iodine reagents was successfully established. This method offers a practical avenue to obtain allyl methyl sulfones and alkenyl by forming C-S bonds. Using C-H bond oxidation sulfonylation strategy Bunte salts, we synthesized total twenty two compounds, including four examples deuterium-substituted molecules, demonstrated one example scale-up reaction.

Language: Английский

Citations

0
Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides DOI Creative Commons
Haifeng Yu, Wanting Zhang, Xuejing Cui

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2225 - 2233

Published: Sept. 3, 2024

An eco-friendly selective hydrolysis of chain α-oxo ketene N , S -acetals in water for the switchable synthesis β-keto thioesters and amides is reported. In refluxing water, reactions presence 1.0 equiv dodecylbenzenesulfonic acid effectively afforded excellent yield, while were successfully obtained yield when carried out 3.0 NaOH. The green approach to avoids use harmful organic solvents, thiols thiolacetates as well amines, which could result serious environmental safety issues.

Language: Английский

Citations

0