Ligand-free copper-catalyzed direct amidation of diaryliodonium salts using nitriles as amidation reagents

Cheng, Hui‐Cheng; Zhou, Lichao; Zhou, Xuming; Ma, Jiaoli; Guo, Ping; Yang, Zhen; Ji, Hongbing

doi:10.1016/j.tetlet.2021.153048

Cited by 7 publications

(6 citation statements)

References 60 publications

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“…For the synthesis of diarylmethane amide derivatives, a novel and simple copper-catalyzed amidation of cyclic diaryliodoniums 1 with commercial nitrile species 77 has been established (Scheme 41). [53][54] With a high atom economy and excellent tolerance, the transformation is effective for a wide range of functional groups on the coupling partners. The fact that nitriles might be selectively arylated without phenyl amino/hydroxyl groups being compromised is remarkable.…”

Section: Cà N Bond Formationmentioning

confidence: 99%

Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis

Cheng

Guo

2023

Adv Synth Catal

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Cyclic diaryliodoniums are an important class of high‐valent aromatic iodine reagents for the synthesis of various axially chiral biaryls and biaryl compounds. Moreover, transition‐metal‐catalyzed annulation has been established for the construction of various heterocyclic rings and ladder‐type π‐conjugated polycyclic aromatic hydrocarbons with readily available cyclic diaryliodoniums as the starting materials. As halogen‐bonding donors, cyclic aryliodoniums have been explored as organocatalysts in a variety of organic reactions. In this review, the application progress of cyclic diaryliodoniums has been systematically outlined, which highlights recent developments in the application reactions of cyclic diaryliodoniums, including synthetic application, limitations and reaction mechanisms in representative cascade reactions to provide insights for the development prospects of cyclic diaryliodoniums.

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Section: Cà N Bond Formationmentioning

confidence: 99%

Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis

Cheng

Guo

2023

Adv Synth Catal

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“…N ‐arylamides can be obtained via the coupling of aryl diazonium tetrafluoroborates [6b] and nitriles (Scheme 1, ex. 1), or via copper‐catalyzed amidation of diaryliodonium salts [6a] or aryl halides [6d] with nitriles (Scheme 1, ex. 2–3).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Approach to Amide Bond Formation

Strekalova,

Kononov,

Morozov

et al. 2023

Adv Synth Catal

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Electrochemical amidation of the C(sp2)−H and C(sp3)−H bonds of broad spectrum of arenes toward the direct synthesis of anilides and N‐benzylamides under mild conditions (room temperature, ambient pressure) in the absence of metal catalyst and external oxidizing agents using nitriles RCN (R=Me, Et) as amide source is described. This electrochemical approach features moderate to high yields, a broad scope of arenes with different functional groups and is amenable to gram scale synthesis. The key role of the hydroxyl radical as inductor generated during the oxidation of water and fixed by a spin trap in EPR experiment has been established.

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“…They are mainly used in the synthesis of pharmaceutical products. [10][11][12] Chemical hydrolysis of nitriles requires the use of strong acids at elevated temperatures, which causes corrosion and disposal problems. 13 One environmentally friendly alternative, however, is enzymatic hydrolysis that can occur via two routes.…”

Section: Introductionmentioning

confidence: 99%

“…Carboxylic acids 6,7 and/or amides are obtained 8,9 from the hydrolysis of nitriles. They are mainly used in the synthesis of pharmaceutical products 10–12 . Chemical hydrolysis of nitriles requires the use of strong acids at elevated temperatures, which causes corrosion and disposal problems 13 .…”

Section: Introductionmentioning

confidence: 99%

High‐throughput screening for distinguishing nitrilases from nitrile hydratases in Aspergillus and application of a Box–Behnken design for the optimization of nitrilase

Santos

Menezes

Santos

et al. 2021

Biotech and App Biochem

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Nitrilases and nitrile hydratases/amidases hydrolyze nitriles into carboxylic acids and/or amides, which are used in industrial chemical processes. In the present study, 26 microorganisms, including yeasts and filamentous fungi, in a minimum solid mineral medium supplemented with glucose and phenylacetonitrile were screened to evaluate their biocatalytic potential. Of these microorganisms, five fungi of the genus Aspergillus were selected and subjected to colorimetry studies to evaluate the production and distinction of nitrilase and nitrile hydratase/amidase enzymes. Aspergillus parasiticus Speare 7967 and A. niger Tiegh. 8285 produced nitrilases and nitrile hydratase, respectively. Nitrilase optimization was performed using a Box–Behnken design (BBD) and fungus A. parasiticus Speare 7967 with phenylacetonitrile volume (μl), pH, and carbohydrate source (starch:glucose; g/g) as independent variables and nitrilase activity (U ml–1) as dependent variable. Maximum activity (2.97 × 10–3 U ml–1) was obtained at pH 5.5, 80 μl of phenylacetonitrile, and 15 g of glucose. A. parasiticus Speare 7967 showed promise in the biotransformation of nitriles to carboxylic acids.

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Ligand-free copper-catalyzed direct amidation of diaryliodonium salts using nitriles as amidation reagents

Cited by 7 publications

References 60 publications

Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis

Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis

Electrochemical Approach to Amide Bond Formation

High‐throughput screening for distinguishing nitrilases from nitrile hydratases in Aspergillus and application of a Box–Behnken design for the optimization of nitrilase

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