Palladium-Catalyzed Denitrative Synthesis of Aryl Nitriles from Nitroarenes and Organocyanides

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3977 - 3981

Опубликована: Апрель 29, 2024

A denitrative cyanation of nitroarenes using organocyanides and a palladium catalyst was developed. The key for this reaction the utilization an aminoacetonitrile as cyano source to avoid generation stoichiometric metal- halogen-containing chemical waste. wide range nitroarenes, including heteroarenes pharmaceutical molecules, can be converted into aryl nitriles.

Язык: Английский

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Transformative Reactions in Nitroarene Chemistry: Advances in C–N Bond Cleavage, Skeletal Editing, and N–O Bond Utilization

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This review aims to provide a comprehensive overview of the expanding utility nitroarenes and their potential for future applications in synthetic organic chemistry.

Язык: Английский

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Direct Synthesis of α-Ketoamides via Copper-Catalyzed Reductive Amidation of Nitroarenes with α-Oxocarboxylic Acids

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6575 - 6583

Опубликована: Апрель 24, 2024

Nitroarenes are known for their stability, low toxicity, easy availability, and cost-effectiveness, making them one of the most fundamental chemical feedstocks. The direct utilization nitroarenes as nitrogen sources in amidation reactions offers significant advantages over using arylamines. Herein, we disclose a streamlined method constructing α-ketoamides through coupling with α-oxocarboxylic acids. This transformation obviates need preparing, isolating, purifying arylamines, leading to improved efficiency, time savings.

Язык: Английский

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Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C–H and C–NO₂ Bond Activations

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7307 - 7312

Опубликована: Авг. 22, 2024

A general approach for the α-arylation of heteroarenes with nitroarenes via denitrative coupling is reported first time. Various heteroarenes, including derivatives furan, benzofuran, pyrrole, indole, thiophene, and benzothiophene, can be arylated at α-position in moderate to good yields. Mechanistic studies demonstrate that reaction proceeds a CMD pathway, C–H bond activation as rate-determining step. Furthermore, scalability applicability synthesis drug molecule exemplify utility this protocol.

Язык: Английский

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Denitrative Functionalization of Nitroarenes: Recent Progress and Future Perspectives

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(45)

Опубликована: Авг. 27, 2024

Abstract Nitroarenes are fundamental feedstocks in the chemical industry. Their relatively inert C−NO 2 bond allows for late‐stage modifications of molecules and exhibits complete orthogonality to reactivity C‐halogen cross‐coupling reactions. The denitrative functionalization nitroarenes holds significant appeal due it avoids use aryl halides, thereby simplifying reaction steps improving atom step economy. Recent progress direct includes palladium‐catalyzed coupling, copper‐catalyzed as well metal‐free one‐pot functionalization. In this review, we provide a concise overview these advancements, detailing features mechanisms. This summary aims highlight versatility efficiency methodologies, offering insights into their potential applications inspiring further research promising area organic synthesis.

Язык: Английский

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Nickel-catalyzed C N bond formation of diarylamine between nitroarenes and aryl Grignard reagents

Journal of Catalysis, Год журнала: 2025, Номер unknown, С. 116050 - 116050

Опубликована: Фев. 1, 2025

Язык: Английский

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Cu-Catalyzed Synthesis of Symmetric Diarylamines from Organoboronic Acids Using NaNO₂ as the Amino Source

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

Опубликована: Март 7, 2025

A copper-catalyzed novel synthesis of symmetric diarylamines was achieved from aryl boronic acids and NaNO2. This protocol employs as the commercially available arylation reagents sodium nitrite (NaNO2) cheap, stable, solid amino source. Under a simple ligand- base-free copper catalytic system (CuCl sole catalyst), wide range could be obtained in moderate to good yields. Notably, use Na15NO2 produce 15N-labeled diarylamines, which would otherwise difficult prepare by known methods.

Язык: Английский

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The terphenyl phosphine TXPhos: A highly efficient and general supporting ligand for palladium-catalyzed C-N cross-coupling of aryl chlorides with diaryl amines as well

Journal of Catalysis, Год журнала: 2025, Номер unknown, С. 116229 - 116229

Опубликована: Май 1, 2025

Язык: Английский

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Palladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 29, 2024

The functionalization of the C-Cl bond in unactivated aryl chlorides under mild conditions presents a significant challenge. We disclose general protocol for constructing both partially and entirely unsymmetrical tertiary phosphines through Pd/keYPhos-catalyzed coupling with secondary conditions. reaction exhibits excellent functional group tolerance broad substrate scopes. Furthermore, rapid synthesis ligands luminescent compound sTPPs, alongside gram-scale systhesis, demonstrates practical applicability this method.

Язык: Английский

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Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 9, 2024

A novel protocol for the Cu-catalyzed reductive

Язык: Английский

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