TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals DOI
Qingsong Liu,

Jiri Gele,

Zhao Kun

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15529 - 15541

Опубликована: Окт. 18, 2024

An efficient TCCA (trichloroisocyanuric acid)/RSeSeR-mediated selenoalkoxy of allenamides for the construction selanyl-allylic N,OA-aminal derivatives was developed. The reaction exhibits good functional group tolerance and high efficiency, affording products in to excellent yields. Mechanistic investigations indicated that a radical intermediate first formed via RSe added central carbon allenamides, which subsequently furnished highly stable carbocation by abstraction an electron chlorine radical. Moreover, this is report using selenium reagent (RSeCl) activate process.

Язык: Английский

Vinylation of Alcohols, Thiols, and Nitrogen Compounds Using a Stoichiometric Amount of In Situ Generated Acetylene DOI Creative Commons
Maria S. Ledovskaya, Vladimir V. Voronin,

А.А. Reznichenko

и другие.

Organics, Год журнала: 2025, Номер 6(1), С. 5 - 5

Опубликована: Фев. 8, 2025

In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of broad scope substances, including alcohols, thiols, nitrogen compounds. The key advantage proposed method is use calcium carbide as robust acetylene source in stoichiometric ratio to substrates. Lacking requirement excess, protocol safe, economic, limits waste production. procedure allows large variety O-,S-,N-vinyl compounds be synthesized up quantitative yields. Our scalable, allowing us obtain vinyl derivatives Gram-scale quantities. We also demonstrated significant synthetic value our approach by performing label-economic synthesis 13C2-labeled using carbide-13C2. well-optimized process, conversion Ca13C2 reached 89%.

Язык: Английский

Процитировано

0
A protocol for selective synthesis of thiol-functionalized allylic sulfonyl fluorides DOI

Monday Peter Ajisafe,

Heba H. Mohamedy,

Eman Fayad

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An efficient and transition metal-free method has been established for synthesizing a class of novel thiol-functionalized allylic sulfonyl fluorides with exclusive regioselectivity.

Язык: Английский

Процитировано

0
TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals DOI
Qingsong Liu,

Jiri Gele,

Zhao Kun

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15529 - 15541

Опубликована: Окт. 18, 2024

An efficient TCCA (trichloroisocyanuric acid)/RSeSeR-mediated selenoalkoxy of allenamides for the construction selanyl-allylic N,OA-aminal derivatives was developed. The reaction exhibits good functional group tolerance and high efficiency, affording products in to excellent yields. Mechanistic investigations indicated that a radical intermediate first formed via RSe added central carbon allenamides, which subsequently furnished highly stable carbocation by abstraction an electron chlorine radical. Moreover, this is report using selenium reagent (RSeCl) activate process.

Язык: Английский

Процитировано

0