Pd(II)‐Catalyzed Selective [4+2] Benzannulations of Pyridones with Alkenes: Diversity‐Oriented Synthesis of a Novel Fluorescent Quinolinone

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

Comprehensive Summary Herein, an intermolecular palladium(II)‐catalyzed regioselective [4+2] benzannulation reaction capable of converting 2‐pyridones into quinolinones was developed using electron‐deficient alkenes as two‐carbon units. An examination the mechanism indicated that extension from 2‐pyridone to quinolinone likely facilitated through a series sequential C—H activation reactions or 6π electrocyclization, culminating in dehydrogenative aromatization. This method diversity‐oriented synthesis derivatives is characterized by broad substrate scope, atom economy, and excellent chemical selectivity. In addition, these exhibit fluorescent absorption within visible‐light spectrum, which makes them suitable candidates for development innovative probes.

Language: Английский

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Co(III)-Catalyzed Three-Component Assembling of 2-Pyridones with Dienes and Formaldehyde via C–H Bond Activation

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

Published: March 24, 2025

Here, we have demonstrated a Co(III)-catalyzed C–H functionalization of substituted pyridones with dienes and para-formaldehyde via three-component sequential reaction. A library homoallylic alcohols is synthesized high regio- chemoselectivity. The reaction scope widely compatible various N-pyridyl-2-pyridones, butadiene, dienes. Interestingly, N-pyridyl-4-pyridone also participated in the product was further converted into dihydrofuran-derived N-pyridyl-2-pyridone derivatives. convincing mechanism mechanistic investigations are described to justify current methodology.

Language: Английский

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Pd-Catalyzed Selective Arylative Cascade Cyclization of 1,6-Diynes and Dibenzoxaborins for Fused Naphthalene Derivatives

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

Published: April 10, 2025

A palladium-catalyzed new mode of cascade arylative cyclization 1,6-diynes is disclosed using dibenzoxaborin as an arylating agent featuring transmetalation and selective migratory insertion the key steps. This process enables efficient construction polysubstituted fused naphthalene skeletons via formation three C-C bonds through dual regioselectivity in both arylation well C-H functionalization. Some control experiments kinetic isotope effect (KIE) studies were conducted to elucidate reaction mechanism, some product diversifications achieved showcase synthetic potential.

Language: Английский

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Ir(III)-Catalyzed Tandem Annulation of Aromatic Amides with 1,6-Diynes via Dual C–H Bond Activation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7809 - 7816

Published: Sept. 10, 2024

An Ir(III)-catalyzed annulation of aryl amides with 1,6-diynes

Language: Английский

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