Rhodium-catalyzed annulation for the construction of indole core: An update

Das, Suven; Dutta, Arpita

doi:10.1016/j.tet.2023.133633

Cited by 4 publications

(2 citation statements)

References 126 publications

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“…[46][47][48] However, during last few years, the use transition-metal as catalyst for obtaining this skeleton has achieved a milestone. [49][50][51][52] In this regard, copper has gained attention as an alternative to precious metals due to its low toxicity, high catalytic activity and cost-effectiveness. In the present review, we highlight recent advances (2019-2023) in copper-catalyzed annulations for the construction of indole motifs.…”

Section: Introductionmentioning

confidence: 99%

“…Various other organocatalytic and metal‐free approaches have also been adopted accordingly [46–48] . However, during last few years, the use transition‐metal as catalyst for obtaining this skeleton has achieved a milestone [49–52] . In this regard, copper has gained attention as an alternative to precious metals due to its low toxicity, high catalytic activity and cost–effectiveness.…”

Section: Introductionmentioning

confidence: 99%

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Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Das,

Dutta

2024

ChemistrySelect

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

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Das,

Dutta

2024

ChemistrySelect

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

Peng,

Doucet,

Soulé

2024

ChemCatChem

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

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Controlling Chemoselectivity in Ruthenium(II)‐Induced Cyclization of Aniline‐Functionalized Alkynes

Io,

Shek,

et al. 2024

Chemistry A European J

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The cyclization of heteroatom‐functionalized alkynes induced by d6‐transition‐metal centers has traditionally been associated with the vinylidene pathway. However, recent evidence suggests that d6‐transition‐metal centers can also activate alkynes through non‐vinylidene pathways. In this study, we conducted a comprehensive experimental and theoretical investigation into the reactions between the Ru(II) complex [Ru([9]aneS3)(bpy)(OH2)]2+ and 2‐alkynylanilines. Our study revealed that the selectivity between the vinylidene and non‐vinylidene pathways can be tuned by reaction temperature, substrate, and solvent polarity. This strategic control allows for the preferential formation of either C2‐ or C3‐metalated indole zwitterion complexes. Additionally, we identified a rare decyclization mechanism that enables the conversion of C2‐metalated indoles to C3‐metalated indoles, underscoring the significance of product stability in these pathways. Overall, this work demonstrates practical approaches to control the preference between vinylidene and non‐vinylidene pathways, which is crucial for the design of new catalysts and metalated heterocyclic complexes.

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Rhodium-catalyzed annulation for the construction of indole core: An update

Cited by 4 publications

References 126 publications

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

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

Controlling Chemoselectivity in Ruthenium(II)‐Induced Cyclization of Aniline‐Functionalized Alkynes

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