Microwave-assisted direct oxidative synthesis of α-ketoamides from aryl methyl ketones and amines by a water soluble Cu(<scp>i</scp>)-complex

Nekkanti, Shalini; Veeramani, Karuna; Kumar, Nitin; Shankaraiah, Nagula

doi:10.1039/c6gc00557h

Cited by 48 publications

(18 citation statements)

References 66 publications

(12 reference statements)

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“…Based on the above results and some relevant publications,,–, a plausible mechanism was proposed, as shown in Figure . With UV at λ=210 nm, molecular oxygen in the air was transformed to ozone (O 3 ), which then underwent gradual dissolution in aqueous media, and decomposed immediately upon meeting with hydroxyl anion (OH − ) to form superoxide radical anion (O 2 .− ), see Figure .…”

Section: Resultsmentioning

confidence: 66%

UV Assisted High‐Efficient Synthesis of α‐Ketoamides using Air Promoted by A Non‐Metal Catalyst in Aqueous Solution

Quan

Shan

et al. 2018

ChemCatChem

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Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α‐ketoamides of all types using a non‐metal catalyst N‐iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.−), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary‐, secondary‐, and tertiary α‐ketoamides were afforded in good to excellent yields of up to 96 %.

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Section: Resultsmentioning

confidence: 66%

UV Assisted High‐Efficient Synthesis of α‐Ketoamides using Air Promoted by A Non‐Metal Catalyst in Aqueous Solution

Quan

Shan

et al. 2018

ChemCatChem

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“…They have concluded that the optimal reaction conditions achieved using catalytic amount (10 mol %) of NiCuFe 2 O 4 nanoparticles (NiCuFe 2 O 4 NPs) in the presence of silica gel, the resulting mixture was heated in a microwave oven at 100 • C for 4 min to obtain the desired products in excellent yields, Scheme 64. Under controlled microwave irradiation technique, Shankaraiah and coworkers have developed novel copper(I)-complex [bis(tetrabutylammonium)di-µ-iodo-diiododicuprate(I)] for the synthesis of α-ketoamides starting from aryl methyl ketones and amines [125]. The reaction proceeds smoothly using a catalytic amount (20 mol %) of the copper(I)-complex (Cu(I)-complex) in the presence of molecular oxygen as oxidizing agent, and water as solvent, the reaction mixture was then heated in a microwave oven at 60 • C for 10 min to produce the target compounds in moderate to excellent yields, Scheme 66.…”

Section: Scheme 62mentioning

confidence: 99%

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

Baqi

2020

Catalysts

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Cross-coupling reactions furnishing carbon–carbon (C–C) and carbon–heteroatom (C–X) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Ullmann, Ullman–Goldberg, Cadiot–Chodkiewicz, Castro–Stephens, and Corey–House, utilizing elemental copper or its salts as catalyst have, for decades, attracted and inspired scientists. However, these reactions were suffering from the range of functional groups tolerated as well as severely restricted by the harsh reaction conditions often required high temperatures (150–200 °C) for extended reaction time. Enormous efforts have been paid to develop and achieve more sustainable reaction conditions by applying the microwave irradiation. The use of controlled microwave heating dramatically reduces the time required and therefore resulting in increase in the yield as well as the efficiency of the reaction. This review is mainly focuses on the recent advances and applications of copper catalyzed cross-coupling generation of carbon–carbon and carbon–heteroatom bond under microwave technology.

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“…Also, the impact of electronic nature of azide and alkyne derivatives in the formation of functionalized 1,2,3‐triazoles cannot be ignored. In the course of time, we identified a stable and isolable, water soluble bis[(tetrabutylammonium) di‐ μ ‐iodo‐diiododicuprate(I)] 71 complex –. We envisioned a Cu(I) catalytic system that would generate 1,2,3‐triazolo‐tetrahydro‐β‐carboline derivatives in excellent yields.…”

Section: 3‐dipolar Cycloadditionmentioning

confidence: 99%

Reliability of Click Chemistry on Drug Discovery: A Personal Account

Shankaraiah

Sakla

Laxmikeshav

et al. 2019

The Chemical Record

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The unprecedented efficiency, reliability and adaptability in drug discovery, with the growing number of applications and impact, have made Click Chemistry fascinating to the scientific community. The specificity, biocompatibility along with other principles of click chemistry offers a reliable platform for the synthesis of drug-like molecules that can expedite the drug discovery process. This account summarizes such successes of versatile click reactions from our research group towards the development of functional molecules.

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Microwave-assisted direct oxidative synthesis of α-ketoamides from aryl methyl ketones and amines by a water soluble Cu(i)-complex

Abstract: A stable and isolable Cu(i) complex has been identified for the direct oxidative synthesis of α-ketoamides in water.

Cited by 48 publications

References 66 publications

UV Assisted High‐Efficient Synthesis of α‐Ketoamides using Air Promoted by A Non‐Metal Catalyst in Aqueous Solution

UV Assisted High‐Efficient Synthesis of α‐Ketoamides using Air Promoted by A Non‐Metal Catalyst in Aqueous Solution

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

Reliability of Click Chemistry on Drug Discovery: A Personal Account

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