Copper‐Catalyzed Regioselective Halogenation of Anilides with <i>N</i>‐Fluorobenzenesulfonimide

Jin, Lianwen; Zeng, Xiaoli; Li, Siyang; Qiu, Guofu; Liu, Peng

doi:10.1002/ejoc.202200399

Cited by 3 publications

(1 citation statement)

References 80 publications

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“…According to the above results, a postulated reaction mechanism is displayed in Scheme . First, the aromatic amine ( 1a ) reacts with alkyl bromide, forming intermediate 1a-1 .…”

Section: Resultsmentioning

confidence: 97%

Copper-Promoted N-Alkylation and Bromination of Arylamines/Indazoles Using Alkyl Bromides as Reagents for Difunctionalization

Wen

Liang

et al. 2022

J. Org. Chem.

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Practical copper-promoted N-alkylation and bromination of arylamines/indazoles with alkyl bromides are described; the N-alkylation-C-4-bromination and N-dialkylation-C-4-bromination of arylamines, and N-alkylation-C-3-bromination of indazoles, with alkyl bromides have been analyzed. The full use of alkyl bromides as alkylating and brominating building blocks without atom wastage, indicating excellent atom and step economy, has been highlighted. Eco-friendly oxygen and water are the reaction oxidant and byproduct, respectively.

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“…According to the above results, a postulated reaction mechanism is displayed in Scheme . First, the aromatic amine ( 1a ) reacts with alkyl bromide, forming intermediate 1a-1 .…”

Section: Resultsmentioning

confidence: 97%

Copper-Promoted N-Alkylation and Bromination of Arylamines/Indazoles Using Alkyl Bromides as Reagents for Difunctionalization

Wen

Liang

et al. 2022

J. Org. Chem.

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Observing the Agostic Hydrogen in Pd(II)-Catalyzed Aromatic C–H Activation

Jiang

Zhang

et al. 2022

J. Org. Chem.

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Direct C−H activation and functionalization offer a convenient protocol for pharmaceutical and material syntheses. Although versatile mechanisms have been proposed to depict transition-metal-catalyzed C−H activation, to date, the shared key agostic hydrogen intermediate in several major mechanisms has not been observed yet, which apparently puzzles the mechanism-based catalyst design. This work reports the direct observations of this intermediate in Pd(II)/Sc(III)-catalyzed C−H activation of acetanilides, and its stability and reactivity in C−H activation are investigated. Remarkably, this intermediate is only observed in electron-rich acetanilides, and the metasubstituent with increased σ m constant generally accelerates C−H activation, a characteristic of the base-assisted C−H activation mechanism. This study has unveiled the masks of this intermediate with an understanding of its first-hand physicochemical properties, shedding new light on mechanism-based catalyst design.

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Electrophilic aromatic substitution of electron-rich arenes with N-fluorobenzenesulfonimide (NFSI) as an electrophile

Bai,

Tu,

Deng

et al. 2024

RSC Adv.

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Copper‐Catalyzed Regioselective Halogenation of Anilides with N‐Fluorobenzenesulfonimide

Cited by 3 publications

References 80 publications

Copper-Promoted N-Alkylation and Bromination of Arylamines/Indazoles Using Alkyl Bromides as Reagents for Difunctionalization

Copper-Promoted N-Alkylation and Bromination of Arylamines/Indazoles Using Alkyl Bromides as Reagents for Difunctionalization

Observing the Agostic Hydrogen in Pd(II)-Catalyzed Aromatic C–H Activation

Electrophilic aromatic substitution of electron-rich arenes with N-fluorobenzenesulfonimide (NFSI) as an electrophile

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