Ligand-Free Cross-Coupling of Boronic Acids with Cu(NO<sub>3</sub>)<sub>2</sub> Complexes of Amines in Aqueous Media

Xu, Jingyi; Li, Jia Rong

doi:10.3184/174751912x13364681530823

Cited by 6 publications

(1 citation statement)

References 43 publications

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“…考虑到这种复合物是固体、在空气中稳定、无味、且具有极好的水溶性, 相对于高挥发性、高刺激性的液态有机胺的使用十分便利, 我们将这类复合物应用于不同底物的氨化反应 [10] , 成功实施了一系列底物的胺化 [11] . 由此我们设想酰胺作为氮源参与构建 C-N 键的转化是否是酰胺键首先发生断裂, 生成的胺与 Lewis 酸形成复合物, 这种复合物再与底物作用得到氨化产物呢?…”

Section: 键的构建是目前有机合成化学的热点之一其中最常见的反应是芳香亲核取代此类反应通常需要强碱、高温 (80～160 )unclassified

Amide as Nitrogen Source： Amination and Mechanism

Xu¹,

Li²,

Wei³

et al. 2013

Chin. J. Org. Chem.

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Section: 键的构建是目前有机合成化学的热点之一其中最常见的反应是芳香亲核取代此类反应通常需要强碱、高温 (80～160 )unclassified

Amide as Nitrogen Source： Amination and Mechanism

Xu¹,

Li²,

Wei³

et al. 2013

Chin. J. Org. Chem.

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Amine, Phenol, Alcohol, and Thiol Arylation

2014

Catalytic Arylation Methods

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Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

et al. 2020

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In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan‐Evans‐Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4‐t‐butyl‐2,5‐bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter‐anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C−N‐bond formation. Forty‐three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C−N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C−N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C−N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).

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Ligand-Free Cross-Coupling of Boronic Acids with Cu(NO₃)₂ Complexes of Amines in Aqueous Media

Cited by 6 publications

References 43 publications

Amide as Nitrogen Source： Amination and Mechanism

Amide as Nitrogen Source： Amination and Mechanism

Amine, Phenol, Alcohol, and Thiol Arylation

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

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Ligand-Free Cross-Coupling of Boronic Acids with Cu(NO3)2 Complexes of Amines in Aqueous Media

Cited by 6 publications

References 43 publications

Amide as Nitrogen Source： Amination and Mechanism

Amide as Nitrogen Source： Amination and Mechanism

Amine, Phenol, Alcohol, and Thiol Arylation

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

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Product

Resources

About

Ligand-Free Cross-Coupling of Boronic Acids with Cu(NO₃)₂ Complexes of Amines in Aqueous Media