Rh-Catalyzed Formal [3 + 2] Cycloaddition Reactions with Cyclopropenones via Sequential C–H/C–C Bond Activation

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

Published: Feb. 13, 2025

The utilization of high-valent metal catalysts to promote cycloaddition reactions involving π bonds through C-C bond activation remains challenging. Despite extensive research, the aldehydes with cyclopropenones catalyzed by complexes has not been documented. Herein, we disclose a novel Rh(III)-catalyzed reaction between and aldehydes, enabling efficient synthesis highly functionalized furanones. A detailed mechanistic investigation was conducted, revealing likely involvement tripodal Rh-carbene intermediate in catalytic cycle, which facilitates product release pathway. This exhibits broad substrate scope, good functional group compatibility, high atom economy, thereby offering versatile general approach construction

Language: Английский

Palladium-Catalyzed Regioselective [3 + 2] Annulation with N-Allenamides at the Proximal C═C Bond: Synthesis of γ-Amino-α′-methylenecyclopentenones

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

Published: April 10, 2025

A palladium-catalyzed [3 + 2] cycloaddition of cyclopropenones with N-allenamides has been developed. This methodology facilitates the synthesis γ-amino-α'-methylenecyclopentenones in moderate to excellent yields good regioselectivity and compatibility various functional groups. The employment as versatile 2C synthons enables simultaneous incorporation both a nitrogen atom methylene group into cyclopentenones. Furthermore, this approach exhibits reverse when compared general allenes. Density theory calculations successfully elucidated origin observed regioselectivity.

Language: Английский

Ag-Catalyzed Selective C–C Bond Activation of Cyclopropenones to Access α-Alkylidene Lactones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6120 - 6124

Published: July 11, 2024

A novel Ag-catalyzed ring opening of unsymmetric cyclopropenones for the stereoselective synthesis a diverse range α-alkylidene lactones has been developed. In this protocol, two different C-C(O) bonds were distinguished, demonstrating selective C-C bond activation. This reaction features wide substrate scope, good functional group compatibility, and high atom economy, providing versatile general approach to construction lactones.

Language: Английский