Copper(I)-catalysed aerobic oxidative selective cleavage of C C bond with DMAP: Facile access to N-substituted benzamides

Ma, Haojie; Lu, Ge; Han, Bo; Huang, Guosheng; Zhang, Yuqi; Wang, Ji‐Jiang

doi:10.1016/j.tetlet.2021.153199

Cited by 5 publications

(3 citation statements)

References 45 publications

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“…Copper salts serve as common catalysts, facilitating reactions with molecular oxygen, primarily involving heterocyclic amines. [180] Less frequent among carboxylic acid derivative functions, notable advancements are found in recent literature. A prime example is the work of Bode and colleagues, which employs potassium acyltrifluoroborates to generate trifluoroborate iminiums (via reaction with an amine), subsequently oxidized using hydrogen peroxide (Figure 38a).…”

Section: Othersmentioning

confidence: 99%

Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out of the thirty‐seven new drugs approved by the FDA in 2022, eleven are small molecules containing at least one amide bond. Additionally, there are nineteen large molecules approved as new drugs, some of which have peptide structures, and therefore, also bear amide bonds. In recent years, multiple teams have embraced the challenge of developing more efficient methods for amide bond formation. This dedication has led to numerous publications appearing monthly in prestigious journals, showcasing significant advancements in this field. The primary goal of this review is to present the most viable strategies for constructing the amide bond. It is crucial to differentiate between amide bond formation and amide synthesis; hence, the focus is on describing specific methods for forming new C(O)−N bonds. In particular, this review concentrates on the methods developed within the last six years. There is a particular emphasis on new approaches that consider the thought process when selecting the starting materials and functional groups. This approach ensures coverage of all the most common chemical transformations that yield new amide bonds.

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Section: Othersmentioning

confidence: 99%

Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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“…Singh’s group reported the synthesis of N -(pyridin-2-yl)amides by the reaction of 2-aminopyridines and ethyl arylacetates via oxidative decarbethoxylation using visible light/CuI/O 2 . Ma et al prepared N -(pyridin-2-yl)amides from aryl ketones and 2-aminopyridine by CuCl/DMAP-mediated oxidative cleavage of the C–C bond . Yadav’s group described the synthesis of N -(pyridin-2-yl)amides by the copper-catalyzed oxidative amidation of aldehydes with 2-aminopyridines in an aqueous micellar system .…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of a Palladium(II) Complex of a C_NHCNN Pincer-Type N-Heterocyclic Carbene Ligand: Application towards the Oxidative Amidation of Aldehydes with 2-Aminopyridines

Swami,

Meena,

Joshi

et al. 2023

Organometallics

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This report describes the synthesis of a [C NHC NN]-pincer-type palladium(II) complex bearing a N-heterocyclic carbene (NHC)-derived pincer CNN ligand. The ligand and palladium pincer complex were characterized with the help of 1 H, 13 C{ 1 H} NMR, Fourier transform infrared (FTIR) spectroscopy, high-resolution mass spectrometry (HRMS), ultraviolet−visible (UV−vis) spectroscopy, and X-ray photoelectron spectroscopy (XPS) techniques. The coordination mode of the ligand with the palladium was confirmed using single-crystal X-ray diffraction studies. The complex possesses a distorted square planar geometry around the palladium center. The Pd(II) pincer complex was used as a catalyst for the oxidative amidation of aldehydes with 2aminopyridines. Notably, only 1.0 mol % catalyst loading is required to activate a wide range of substrates under mild reaction conditions. The protocol showed excellent tolerance toward a diverse range of functional groups with good to very good yields (up to 88%) of amidation products. A plausible mechanism of the amidation reaction is proposed on the basis of control experiments.

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“…[35,36] The development of synthetic methods of amide bond are the greater challenges of chemical synthesis. [37] In recently, there are some replacement methods for synthesis of amide bond, [38] like the acylation reaction of isoxazoline, [39] the reaction of stereoselective ring expansion by attractive cation interaction, [40] the rearrangement of ketoximes to lactams by triphosphazene catalyst, [41] the dual role of aminocarbonylation of aryl cholrides, [42] the formation carbon-nitrogen bond by nitroalkanes as acyl anion, [43] direct amide synthesis from alcohols and amines by the extrusion of dihydrogen, [44] the amidation reaction from esters and amines under neutral conditions, [45] iron-catalysed coupling of nitriles with amines or alcohols, [46] synthesis of amides from alkynyl bromes, amines, and water, [47] the thioacid/azide amidation reaction, [48] transamidation reaction from primary amides and amines [49] and the amidation of alcohols or aldehydes. [50] However, most of these methods have several drawbacks like high cost of catalysts, difficult reaction conditions, limited of derivatives.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of N‐Pyridinylamides Using a Bimetallic Co/Fe‐Metal‐Organic Framework Heterogeneous Catalyst

Nguyen,

Nong,

Nguyen

et al. 2023

ChemistrySelect

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The synthesis of N‐pyridinylamides has been realized by particularly efficient technologies via bimetallic organic (Co/Fe‐MOF) catalyzed oxidative amidation between 2‐aminopyridine and benzaldehyde. The C−N bond was formed with the presence of a catalyst (Co/Fe‐MOF) as a Lewis acid and the oxidant as DTBP. The oxidative amidation reaction was conducted in 1,4‐dioxane at 120 °C with a wide range of substrates producing the corresponding amide products in good to 94 % yields. Experimental results illustrated that This accessibly offers a significant improvement over the earlier successful attempts in forming N‐pyridinyl amides. The Co/Fe‐MOF material was synthesized by solvothermal methods with the salt mixture of Fe(NO3)3.9H2O and Co(NO3)2.6H2O. The material was determined by modern analytic methods like X‐ray diffraction (XRD), Fourier‐transform Infrared spectroscopy (FT‐IR), Scanning Electron Microscope (SEM), and N2 adsorption/desorption isotherms.

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Copper(I)-catalysed aerobic oxidative selective cleavage of C C bond with DMAP: Facile access to N-substituted benzamides

Cited by 5 publications

References 45 publications

Contemporary Approaches for Amide Bond Formation

Contemporary Approaches for Amide Bond Formation

Design and Synthesis of a Palladium(II) Complex of a C_NHCNN Pincer-Type N-Heterocyclic Carbene Ligand: Application towards the Oxidative Amidation of Aldehydes with 2-Aminopyridines

Efficient Synthesis of N‐Pyridinylamides Using a Bimetallic Co/Fe‐Metal‐Organic Framework Heterogeneous Catalyst

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Copper(I)-catalysed aerobic oxidative selective cleavage of C C bond with DMAP: Facile access to N-substituted benzamides

Cited by 5 publications

References 45 publications

Contemporary Approaches for Amide Bond Formation

Contemporary Approaches for Amide Bond Formation

Design and Synthesis of a Palladium(II) Complex of a CNHCNN Pincer-Type N-Heterocyclic Carbene Ligand: Application towards the Oxidative Amidation of Aldehydes with 2-Aminopyridines

Efficient Synthesis of N‐Pyridinylamides Using a Bimetallic Co/Fe‐Metal‐Organic Framework Heterogeneous Catalyst

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Design and Synthesis of a Palladium(II) Complex of a C_NHCNN Pincer-Type N-Heterocyclic Carbene Ligand: Application towards the Oxidative Amidation of Aldehydes with 2-Aminopyridines