Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution

Wang, Jin; Hou, Huiqing; Hu, Yongzhi; Lin, Jin; Wu, Min; Zheng, Zhiqiang; Xu, Xing‐You

doi:10.1016/j.tetlet.2020.152801

Cited by 8 publications

(8 citation statements)

References 63 publications

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“…Accordingly, novel amidation protocols have been reported in recent years which avoid the use of toxic, sensitizing, and atom inefficient coupling reagents . These methods include the amidation of carboxylic acids via the corresponding acyl fluorides or by the direct condensation of unactivated carboxylic acids with amines using silicon reagents or utilizing boron, transition metal, or photoredox catalysis . Alternative strategies involve the direct amidation of esters, the oxidative amidation of aldehydes, or palladium-catalyzed carbonylation of aryl halides …”

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confidence: 99%

Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds

et al. 2022

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We report the use of N-2,4-dinitrophenyltetrazoles as latent active esters (LAEs) in the synthesis of amide bonds. Activating the tetrazole generates an HOBt-type active ester without the requirement for exogenous coupling agents. The methodology was widely applicable to a range of substrates, with up to quantitative yields obtained. The versatility and functional group tolerance were exemplified with the one-step synthesis of various pharmaceutical agents and the N-acylation of resin-bound peptides.

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confidence: 99%

Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds

et al. 2022

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“…Recently, a sunlight-driven iodine-catalyzed synthesis of amides 92 from amines 27 and carboxylic acids 13 was achieved by Xu and co-workers (Scheme 42). 104 Aromatic amines possessing a variety of functional groups including OH, OMe, Cl, NO 2 , etc ., delivered the respective amides in good yields. Besides, aliphatic acyclic amines (primary and secondary) also displayed good compatibility under the given reaction conditions.…”

Section: Photocatalyst-free Strategiesmentioning

confidence: 99%

Green and sustainable visible light-mediated formation of amide bonds: an emerging niche in organic chemistry

Singh

Sharma

2022

New J. Chem.

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“…Understanding the influence of substituents on the properties of amide compounds is crucial for tailoring their reactivity, stability, and interactions. Incorporating different groups enables the modulation of their chemical and physical properties, such as polarity, electronic effects, and steric hindrance [4b,5a,9] . This provides opportunities for designing and developing novel amide‐based materials with customized properties [10] .…”

Section: Introductionmentioning

confidence: 99%

Exploring Structural and Spectroscopic Properties of Secondary Amide Derivatives Bearing Bulky and Hydrophilic Substituents

Nossa González,

Gómez Castaño,

Franca

et al. 2023

ChemistrySelect

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The synthesis of four novel amide compounds (R1C(O)NHR2) is reported, which contain both bulky (R1=phenyl and adamantyl) and hydrophilic (R2=hydroxyl, methoxyl) groups. The incorporation of such substituents provides compounds with unique properties that combine steric hindrance and hydrophilicity. The synthesized amides were fully characterized by 1H and 13C nuclear magnetic resonance (NMR) and analysed using infrared (IR) and Raman spectroscopy to investigate their vibrational properties in the solid phase, specifically focusing on the amide‐type normal modes of vibrations. Furthermore, the crystal structures of three derivatives were determined by single‐crystal X‐ray diffraction, which provided insights into their molecular arrangements. The occurrence of N−H⋅⋅⋅O=C hydrogen bonding intermolecular interaction is clearly observed and characterized by Hirschfeld surface analysis. Topology analysis using the Quantum Theory of Atom in Molecules and Crystals (QTAIM−C) were employed to investigate the electronic properties of the isolated amide molecules and to analyse the intermolecular interactions within the crystalline structure. The periodic calculations for the crystal revealed a higher electronic density in the C−N bond, indicating an increased covalent character in this bond compared with the C=O bond. This observation indicates the presence of resonance‐assisted hydrogen bonds within the amide core, leading to π electronic delocalization.

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Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution

Cited by 8 publications

References 63 publications

Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds

Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds

Green and sustainable visible light-mediated formation of amide bonds: an emerging niche in organic chemistry

Exploring Structural and Spectroscopic Properties of Secondary Amide Derivatives Bearing Bulky and Hydrophilic Substituents

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