An Effective Heterogeneous Copper Catalyst System for C–N 
Coupling and Its Application in the Preparation of 
2-Methyl-4-methoxydiphenylamine (MMDPA)

Zhou, Yi; Huang, Manna; Wan, Yiqian; Zhu, Xinhai

doi:10.1055/s-0037-1609578

Cited by 9 publications

(1 citation statement)

References 15 publications

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“…This coupling product is a common intermediate for production of the aminofluoran dye for thermographic and pressure-sensitive recording (Scheme 4a(III)). 21 Treatment of 3-(trifluoromethyl)aniline with 1s yielded 3sv in 61% yield. Subsequent base hydrolysis produced the nonsteroidal antiinflammatory drug flufenamic acid in 90% yield (Scheme 4a (IV)).…”

Section: Resultsmentioning

confidence: 99%

Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

Zhu,

Li,

Young

et al. 2023

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

Zhu,

Li,

Young

et al. 2023

Org. Chem. Front.

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Direct Synthesis of Diphenylamines from Phenols and Ammonium Formate Catalyzed by Palladium

Dominguez‐Huerta

Perepichka

2019

ChemSusChem

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Arylamines are commerciallya nd synthetically useful compounds with aw ide variety of applications.T heir preparation has been traditionally achieved using metal-catalyzedC ÀN coupling reactions with aryl halides. In this work, 17 different diarylamines are prepared from phenolsb yu sing ammonium formate as the aminatingr eagent. Phenolicc ompounds are more desirable feedstocks, owing to their availability from lignin, making them valuable biorenewable alternatives to aryl halides. Ammonium formate is found to be aconvenient surrogate for ammonia and au seful aminating reagent for phenols. Diarylamine products are obtained in good to excellent yields while only water and CO 2 are generated as byproducts of the transformation.Arylamines are valuable commodity chemicals, owing to their broad application as antioxidizers and as synthetically relevant buildingblocks. Diphenylamine (DPA) is primarily used as astabilizer for nitrocellulose explosives [1] and the detection of oxidizers, [2] whereas C-alkylated diphenylamines are widely used as antioxidants for the preservation of fruits, [3] oils, [4] and polymers. [5] Further uses of arylamines include being ap recursor for the synthesis of (azo-)dyes, [6] and nonsteroidal anti-inflammatoryd rugs. [7] Additionally,t riphenylamines are important for the preparation of optoelectronic materials. [8] For at horough review on the use of these compounds, please see the reference articles by Drzyzga [9] and Layer. [10] Arylamines are commonly prepared from amine precursors through metal-catalyzedC ÀNc oupling reactions. Methods for the formation of these compounds include the Stille, [11] Chan-Evans-Lam, [12] Ullmann, [13] and Buchwald-Hartwig [14] couplings. In addition, other methods, including P III /P V =Oc atalysis, [15] iodine, [16] sulfonium triflates, [17] various nanoparticle catalysts, [18] and Pd/C catalysis for the formationo fa rylamines from aliphatic substrates, [19] have also been reported. Similard evelopments for the formation of diaryl ethers have also been reported. [20] Phenol can be obtainedf rom naturals ources, as one of the basic units of lignin, making it an attractive biorenewable feed-

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Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp²)−N Bond Construction

Lei

Xie

et al. 2021

Eur J Org Chem

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N‐Aryl‐ and N‐alkenylhydrazides, which include a C(sp2)‐N−N motif, have attracted considerable attention not only in biologically active molecules but also because of their extensive technical applications in organic synthesis. C(sp2)−N bond construction protocols using an N‐acylhydrazine or azocarboxylic ester as the hydrazide source provide a powerful route to these compounds. These protocols exhibit different selectivity manner for the C(sp2) moiety and the regioselectivity issue of the N−N bond. This Minireview documents the available methods that have been developed based on different starting materials. The features and drawbacks of each subdivisional methodology are demonstrated.

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An Effective Heterogeneous Copper Catalyst System for C–N Coupling and Its Application in the Preparation of 2-Methyl-4-methoxydiphenylamine (MMDPA)

Cited by 9 publications

References 15 publications

Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

Direct Synthesis of Diphenylamines from Phenols and Ammonium Formate Catalyzed by Palladium

Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp²)−N Bond Construction

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An Effective Heterogeneous Copper Catalyst System for C–N Coupling and Its Application in the Preparation of 2-Methyl-4-methoxydiphenylamine (MMDPA)

Cited by 9 publications

References 15 publications

Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

Direct Synthesis of Diphenylamines from Phenols and Ammonium Formate Catalyzed by Palladium

Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp2)−N Bond Construction

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Product

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Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp²)−N Bond Construction