One-pot synthesis of N,N-dimethylanilines from nitroarenes with skeletal Cu as chemoselective catalyst

Rong, Zeming; Zhang, Wenjun; Zhang, Peng; Sun, Zhuohua; Lv, Jinkun; Du, Wentao; Wang, Yue

doi:10.1016/j.catcom.2013.07.023

Cited by 20 publications

(10 citation statements)

References 19 publications

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“…(1) reaction of amines with methylating reagents such as methyl halides, dimethyl sulfate, 6 dimethyl carbonate, 7 dimethyl sulfoxide (DMSO) 8 and so on; (2) reductive amination reaction of formaldehyde [9][10][11] and (3) N-methylation of amines with carbon dioxide and molecular hydrogen. [12][13][14] Unfortunately, these methods are oen problematic from synthetic or environmental standpoints.…”

Section: Introductionmentioning

confidence: 99%

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO₂ at room temperature

Zhang

Deng

et al. 2015

RSC Adv.

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A series of TiO 2 supported nano-Pd catalysts (Pd/TiO 2 ) were prepared and used for the N,N-dimethylation of different amines and nitro compounds with methanol under UV irradiation at room temperature. A wide range of N,N-dimethyl amines were one-pot synthesized with up to 98% by applying aliphatic secondary amines, aromatic primary amines, aliphatic primary amines and aromatic nitro compounds as starting materials. It is noteworthy that up to 90% yield of 4-chloro-N,N-dimethylaniline was obtained by adjusting the Pd loadings on the TiO 2 and the dehalogenation reaction was inhibited. Finally, a reaction mechanism is discussed, involving PhN ¼ CH 2 and PhNHCH 3 as reaction intermediates.

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Section: Introductionmentioning

confidence: 99%

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO₂ at room temperature

Zhang

Deng

et al. 2015

RSC Adv.

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“…Methanol served as a hydrogen source, alkylating reagent, and solvent simultaneously. Several years later, Rong and co-workers reported the one-pot synthesis of N , N -dimethyl anilines with HCHO and nitroarenes catalyzed by the quenched skeletal Cu catalyst. Many N , N -dimethyl aniline products were obtained in good to excellent selectivity under the optimized reaction condition (nitroarenes: 6 mmol, HCHO: 18 mmol, 0.5 g skeletal Cu catalyst, 13 bar H 2 , 70–100 °C, 37–127 min).…”

Section: Introductionmentioning

confidence: 99%

N-Dimethylation and N-Functionalization of Amines Using Ru Nanoparticle Catalysts and Formaldehyde or Functional Aldehydes as the Carbon Source

Liu

Song

et al. 2021

ACS Omega

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N-methylated amines are essential bioactive compounds and have been widely used in the fine and bulk chemical industries, as well as in pharmaceuticals, agrochemicals, and dyes. Developing green, efficient, and low-cost catalysts for methylation of amines by using efficient and easily accessible methylating reagents is highly desired yet remains a significant challenge. Herein, we report the selective N-dimethylation of different functional amines with different functional aldehydes under easy-to-handle and industrially applicable conditions using carbon-supported Ru nanoparticles (Ru/C) as a heterogeneous catalyst. A broad spectrum of amines could be efficiently converted to their corresponding N,N-dimethyl amines with good compatibility of various functional groups. This method is widely applicable to N-dimethylation of primary amines including aromatic, aliphatic amines with formaldehyde, and synthesis of tertiary amines from primary, secondary amines with different functional aldehydes. The advantage of this newly described method includes operational simplicity, high turnover number, the ready availability of the catalyst, and good functional group compatibility. This Ru/C catalyzed N-dimethylation reaction possibly proceeds through a two-step N-methylation reaction process.

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“…The methanol was served as a hydrogen source, alkylating reagent and solvent simultaneously. Several years later, Rong and co-workers 21 reported the one-pot synthesis of N, N-di-methyl anilines with HCHO and nitroarenes catalyzed by the quenched skeletal Cu catalyst. Many N, N-dimethyl anilines products were obtained in good to excellent selectivity under the optimized reaction condition (nitroarenes: 6 mmol, HCHO: 18 mmol, 0.5 g skeletal Cu catalyst, 13 bar H 2 , 70-100 °C, 37-127 min).…”

Section: Introductionmentioning

confidence: 99%

Efficient and Selective N-Dimethylation of Amines with Functional Aldehydes Catalysed by Ru Nanoparticles Heterogeneous Catalyst

Liu

Song²,

Wang³

et al. 2021

Preprint

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<p>N-methylated amines are essential bioactive compounds and have been widely used in the fine and bulk chemical industries, as well as in pharmaceuticals, agrochemicals, and dyes. Developing green, efficient, and low-cost catalysts for methylation of amines by using efficient and easily accessible methylating reagents is highly desired yet remains a significant challenge. Herein, we report the selective N-dimethylation of different functional amines with different functional aldehydes under easily handle-able and industrially applicable conditions using carbon-supported Ru nanoparticles (Ru/C) as a heterogeneous catalyst. A broad spectrum of amines could be efficiently converted to their corresponding N, N-dimethyl amines with good compatibility of various functional groups. This method is widely applicable to N-dimethylation of primary amines including aromatic, aliphatic amines with formaldehyde, and synthesis of tertiary amines from primary, secondary amines with different functional aldehydes. The advantage of this newly described method includes operational simplicity, high turnover number, the ready availability of the catalyst, and good functional group compatibility. This Ru/C catalyzed N-dimethylation reaction possibly proceed through a twice N-methylation reaction process.</p>

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One-pot synthesis of N,N-dimethylanilines from nitroarenes with skeletal Cu as chemoselective catalyst

Cited by 20 publications

References 19 publications

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO₂ at room temperature

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO₂ at room temperature

N-Dimethylation and N-Functionalization of Amines Using Ru Nanoparticle Catalysts and Formaldehyde or Functional Aldehydes as the Carbon Source

Efficient and Selective N-Dimethylation of Amines with Functional Aldehydes Catalysed by Ru Nanoparticles Heterogeneous Catalyst

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One-pot synthesis of N,N-dimethylanilines from nitroarenes with skeletal Cu as chemoselective catalyst

Cited by 20 publications

References 19 publications

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO2 at room temperature

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO2 at room temperature

N-Dimethylation and N-Functionalization of Amines Using Ru Nanoparticle Catalysts and Formaldehyde or Functional Aldehydes as the Carbon Source

Efficient and Selective N-Dimethylation of Amines with Functional Aldehydes Catalysed by Ru Nanoparticles Heterogeneous Catalyst

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Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO₂ at room temperature

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO₂ at room temperature