Vinylation of Alcohols, Thiols, and Nitrogen Compounds Using a Stoichiometric Amount of In Situ Generated Acetylene

Organics, Journal Year: 2025, Volume and Issue: 6(1), P. 5 - 5

Published: Feb. 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%.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15529 - 15541

Published: Oct. 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.

Language: Английский