Assembly of Diverse Allenes via Activator-Free Palladium-Catalyzed Regioselective γ-Arylation of Propargylamines with Boronic Acids

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

Published: Feb. 7, 2025

Controlling the reaction selectivity to achieve a precision synthesis is constant concern for chemists. Here, we report palladium-catalyzed deaminative coupling of propargylamines with arylboronic acids generate allene skeletons. Importantly, this approach allows regioselective γ-arylation unactivated propargyl tertiary amines access various allenes in absence amino-activating reagents. We present wide range and boronic demonstrate synthetic application target products construct valuable compounds.

Language: Английский

Difluorocarbene-Enabled Dehydration of Primary Amides To Access Nitriles

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

Published: March 16, 2025

A cost-effective and environmentally friendly method for the direct conversion of primary amides to nitriles was developed using commercially available non-toxic ethyl bromodifluoroacetate as a difluorocarbene precursor under metal-free ligand-free conditions. The reaction features high yields tolerates various sensitive moieties, including alkyl, alkenyl, ether, sulfone, sulfoxide, heteroaryl, chloro, bromo, iodo, hydroxyl, nitro, cyano groups, late-stage modification complex molecules is also feasible. Moreover, present effective on large scales, showing potential industrial application.

Language: Английский

C(sp3) P cross-coupling of alkyl substrates with P(O) H compounds and phosphites

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 149, P. 155266 - 155266

Published: Aug. 22, 2024

Language: Английский