Regioselective copper-catalyzed amination of halobenzoic acids using aromatic amines

Maradolla, Mohan Babu; Amaravathi, M.; Kumar, Virendra; Mouli, G. V. P. C.

doi:10.1016/j.molcata.2006.10.017

Cited by 10 publications

(5 citation statements)

References 28 publications

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“…Regioselective synthesis of N‐arylanthranilic acid by amination of o ‐halobenzoic acids using copper catalyst was reported by Garimella and co‐workers . The reaction between aromatic amines and 2‐halobenzoic acids were performed using CuPy 2 Cl 2 and afforded the expected products with different substituents in good to excellent yields ( Scheme ) .…”

Section: Amination Using Alkylamine or Anilinementioning

confidence: 99%

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

et al. 2020

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Section: Amination Using Alkylamine or Anilinementioning

confidence: 99%

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

et al. 2020

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“…Literature procedures were followed to synthesize NBAs (Scheme ). Synthetic details can be found in the Supporting Information (SI).…”

Section: Methodsmentioning

confidence: 99%

Effect of Substituent Size and Isomerization on the Polymorphism of 2-(Naphthalenylamino)-benzoic Acids

Liu

Zhang

et al. 2019

Crystal Growth & Design

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To probe the effect of substituent size and isomerization on the polymorphism of fenamic acid (FA) derivatives, we synthesized two FA analogues, namely, 2-(naphthalen-1-ylamino)-benzoic acid and 2-(naphthalen-2-ylamino)-benzoic acid (NBAs), and investigated their polymorphism. Contrary to the lack of polymorphism in FA, we discovered two crystal forms (1-I, 1-II, 2-I, and 2-II) for each of the two compounds. We characterized the two polymorphic systems with single-crystal X-ray diffraction, powder X-ray diffraction, and infrared and Raman spectroscopy, and observed certain structural similarities between 1-I and 2-I. The phase behavior of these two systems were studied with differential scanning calorimetry. Computational studies such as the search for stable conformers, lattice-energy calculations, and Hirshfeld surface analysis were performed to shed light on the polymorphism, relative stability of the forms in each system, and contribution of intermolecular interactions to the overall stability of the systems. The study confirmed the effect of substituent size on the polymorphism of the compounds.

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“…In addition, 2-Chlorobenzoic is another well-known and often applied Ar-Cl-based arylating agent containing a carboxyl group in the role of Ewg. However, 2-chlorobenzoic acid requires the application of a Cu-based catalyst for effective C-N cross-coupling [74][75][76][77].…”

Section: Cu-catalyzed Substitution Of Halogen In Ar-xs With Primary A...mentioning

confidence: 99%

“…N,N -Dimethylcyclohexane-1,2-diamine DMCHDA (Figure 2) was proved to be an effective ligand for amidation of aryl chlorides used in excess as both arylation agents and solvent with the addition of CuI and K 3 PO 4 at 130 In addition, 2-Chlorobenzoic is another well-known and often applied Ar-Cl-based arylating agent containing a carboxyl group in the role of Ewg. However, 2-chlorobenzoic acid requires the application of a Cu-based catalyst for effective C-N cross-coupling [74][75][76][77].…”

Section: Cu-catalyzed Substitution Of Halogen In Ar-xs With Primary A...mentioning

confidence: 99%

Copper-Catalyzed Reactions of Aryl Halides with N-Nucleophiles and Their Possible Application for Degradation of Halogenated Aromatic Contaminants

2022

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This review summarizes recent applications of copper or copper-based compounds as a nonprecious metal catalyst in N-nucleophiles-based dehalogenation (DH) reactions of halogenated aromatic compounds (Ar-Xs). Cu-catalyzed DH enables the production of corresponding nonhalogenated aromatic products (Ar-Nu), which are much more biodegradable and can be mineralized during aerobic wastewater treatment or which are principally further applicable. Based on available knowledge, the developed Cu-based DH methods enable the utilization of amines for effective cleavage of aryl-halogen bonds in organic solvents or even in an aqueous solution.

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Regioselective copper-catalyzed amination of halobenzoic acids using aromatic amines

Cited by 10 publications

References 28 publications

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

Effect of Substituent Size and Isomerization on the Polymorphism of 2-(Naphthalenylamino)-benzoic Acids

Copper-Catalyzed Reactions of Aryl Halides with N-Nucleophiles and Their Possible Application for Degradation of Halogenated Aromatic Contaminants

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