Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Miao, Yuqi; Kang, Jiaxin; Ma, Yan‐Na; Chen, Xuenian

doi:10.1039/d1gc01157j

Cited by 33 publications

(30 citation statements)

References 49 publications

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“…To our delight, a good yield of product 3a was produced while using toluene as a solvent (entry 11). Meanwhile, we checked the effect of temperature on the reaction, and it was found that rising or falling the temperature will reduce the yield of product 3a (entries [12][13][14]. Then, Then, the loading effects of the oxidant were explored.…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

“…Flash column chromatography was generally performed on silica gel (200-300 mesh) and the progress of the reaction was monitored by thin-layer Template for SYNTHESIS Thieme chromatography (TLC). NMR spectra ( 1 H NMR at 400 MHz, 13 C NMR at 100 MHz) were recorded on a Bruker Inova-400 instrument using tetramethylsilane (TMS) as an internal standard, chemical shifts (in ppm) were referenced to CDCl3 (δ=7.26 ppm). High-resolution mass spectrometry (HRMS) data were performed at a Micromass Q-TOF Global Tandem Mass Spectrometer.…”

Section: Scheme 3 Mechanistic Studymentioning

confidence: 99%

“…1 H NMR (400 MHz, DMSO-d6) δ 10.12 (s, 1H), 7.98-7.92 (m, 2H), 7.68 (d, J=9.0 Hz, 2H), 7.58 (t, J=7.2 Hz, 1H), 7.52 (t, J=7.3 Hz, 2H), 6.93 (d, J=9.0 Hz, 2H), 3.75 (s, 3H). 13…”

Section: N-(p-tolyl)benzamide (3a)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl3) δ 9.18 (s, 1H), 8.84-8.78 (m, 2H), 8.42 (dt, J=8.4, 1.0 Hz, 1H), 8.27 (ddd, J=5.0, 1.9, 0.9 Hz, 1H), 7.86-7.80 (m, 1H), 7.80-7.77 (m, 2H), 7.18-7.09 (m, 1H). 13…”

Section: N-(pyridin-2-yl)isonicotinamide (3g) 20mentioning

confidence: 99%

“…12 Recently, Chen et al reported a new method to obtain functionalized amide via available amine boranes and carboxylic acid in the presence of photocatalyst. 13 In 2021, Zou et al developed a new protocol for the synthesis of carbamates via amines with alkoxycarbonyl in the coppercatalyzed system (Scheme 1c). 14 It is noteworthy that Liu et al developed an advanced approach as manganese catalyzed amidation reaction from fatty acid esters and amines (Scheme 1d).…”

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confidence: 99%

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Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation

Li¹,

Zhang²,

Ablajan³

2022

Synthesis

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An efficient protocol for the amidation of hydrazide with amine has been developed by utilizing I2 as an oxidant under metal and base-free conditions at room temperature. N-acylation products of amines were obtained in good to excellent yield without using toxic reagents. This method is operationally straightforward and tolerates aliphatic/aromatic and primary/secondary amines with different hydrazides.

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Section: Template For Synthesis Thiemementioning

confidence: 99%

Section: Scheme 3 Mechanistic Studymentioning

confidence: 99%

“…1 H NMR (400 MHz, DMSO-d6) δ 10.12 (s, 1H), 7.98-7.92 (m, 2H), 7.68 (d, J=9.0 Hz, 2H), 7.58 (t, J=7.2 Hz, 1H), 7.52 (t, J=7.3 Hz, 2H), 6.93 (d, J=9.0 Hz, 2H), 3.75 (s, 3H). 13…”

Section: N-(p-tolyl)benzamide (3a)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl3) δ 9.18 (s, 1H), 8.84-8.78 (m, 2H), 8.42 (dt, J=8.4, 1.0 Hz, 1H), 8.27 (ddd, J=5.0, 1.9, 0.9 Hz, 1H), 7.86-7.80 (m, 1H), 7.80-7.77 (m, 2H), 7.18-7.09 (m, 1H). 13…”

Section: N-(pyridin-2-yl)isonicotinamide (3g) 20mentioning

confidence: 99%

mentioning

confidence: 99%

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Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation

Li¹,

Zhang²,

Ablajan³

2022

Synthesis

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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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Organophotocatalytic Carbamoylation of Morita‐Baylis‐Hillman Carbonates

Marchini,

Vélez,

Andre

et al. 2024

Adv Synth Catal

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The synthesis and modification of structures containing the amide functionality play a significant role in the development of pharmaceuticals and biologically active compounds. While conventional amidation strategies primarily relies on C‐N bond formation, the strategic integration of photoredox catalysis for synthesizing these compounds through C‐C bond formation is in accordance with the principles of green chemistry and sustainability. Herein, we demonstrate that carbamoyl radicals generated through an organophotocatalytic protocol from 4‐carbamoyl‐dihydropyridines (carbamoyl‐DHPs) can be incorporated into Morita‐Baylis‐Hillman (MBH) carbonates, affording a range of polyfunctionalized scaffolds. Reaction monitoring experiments, scale‐up, reuse of the organophotocatalyst, and the hydrogenation of the succinamic ester´s alkene moiety was also conducted, in order to showcase the mechanistic features and the robustiness of this new photochemical protocol.

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Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Abstract: A practical method for the amidation reaction between carboxylic acids and amines was developed, for the first time, through a visible light-mediated photoredox deoxygenation at room temperature.

Cited by 33 publications

References 49 publications

Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation

Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation

Contemporary Approaches for Amide Bond Formation

Organophotocatalytic Carbamoylation of Morita‐Baylis‐Hillman Carbonates

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