Electron-Deficient CpRh(III)-Catalyzed C–H Functionalization of N-2-Pyridylanilines: Branch-Selective Alkenylation with Alkenes and Annulation with Alkynes

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

We report the electron-deficient CpRh(III) [CpERh(III)] complex-catalyzed branch selective alkenylation with aliphatic alkenes and annulation internal alkynes using N-2-pyridylanilines. In these reactions, CpERh(III) catalyst is more active than electron-rich Cp*Rh(III) catalyst, used commonly in C–H activation, reactions proceed a catalytic amount of Cu(II) oxidant under air at lower temperatures conventional methods. From mechanistic considerations, steric repulsion between ligand directing group may be responsible for alkenylation.

Язык: Английский

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Rhodium‐Catalyzed C–H Bond Annulation for the Synthesis of 5‐ and 6‐Membered N‐Heterocyclic Building Blocks

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Май 17, 2024

Abstract The sustainable preparation of N ‐heterocycles is one the most active research areas owing to their predominance as synthetics building blocks with extensive applications in organic, pharmaceutical, and material chemistry fields. Among various catalytic protocols, C−H bond functionalization concomitant C−N formation, so‐called annulation, has become routes access because it starts from low‐functionalized materials generates a limited amount waste, all respecting concept atom economy. Rhodium complexes often catalyze these reactions. This review focuses on synthesis 5‐ 6‐membered ring ‐containing heterocycles such indoles, pyrroles, indolines, (iso)quinolinones, dihydroquinolines, pyrrolidones readily available starting materials, an emphasis novel cascade synthetic methodologies via C−N/C−C well mechanisms reactions, especially oxidation steps. We hope this will help researchers looking prepare minimum steps those who want develop new based activation/functionalizations.

Язык: Английский

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Copper–Catalyzed Construction of the Indole Core: Recent Advancements

ChemistrySelect, Год журнала: 2024, Номер 9(7)

Опубликована: Фев. 13, 2024

Abstract Indoles are one of the most important heterocycles because their widespread occurrence in bioactive natural products, synthetic drugs and organic materials. Therefore, development efficient strategies for synthesizing functionalized indoles has been great importance synthesis. Copper, being a transition metal, meet goal due to its low toxicity, high catalytic activity cost‐effectiveness. In this review, we focus on last five year (2019–2023) advancement copper‐catalyzed annulations construction indole core involving various N‐containing substrates, which include anilines, o ‐alkynylanilines, ‐aminophenylpropynols, ‐alkynylnitroarenes, ‐nitrochalcones, azidoalkynes, isonitriles, nitriles, enamines, imines, etc. Mechanistic aspects reactions have also highlighted better understanding reaction pathways.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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