Copper/manganese oxide catalyzed regioselective amination of quinoline N-oxides: An example of synergistic cooperative catalysis

Sahoo, Tapan; Thakur, Dinesh; Panda, Asit Baran; Ghosh, Subhash

doi:10.1016/j.tetlet.2021.153415

Cited by 3 publications

References 35 publications

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Recent Advances and Prospects in Manganese‐Catalyzed C−H Activation

Anusree,

Devi,

Anilkumar

2024

Adv Synth Catal

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C–H activation represents an interesting alternative to conventional cross‐coupling methods, avoiding the requirement of additional steps to introduce activating groups. Generally, Pd‐catalyzed reactions have been extensively employed for C–H activation. The high cost and limited availability of resources of Pd have prompted us to explore alternative transition metals. In this context, researchers are turning to Earth Abundant Metals (EAMs) like manganese and iron for their potential in C–H activation.Significant progress has been made in manganese‐catalyzed C–H activation in recent years, showcasing excellent specificity, environmental compatibility, and versatility across different substrates. This review summarizes approximately 50 recent publications highlighting significant advancements in this field from 2020 to 2023.

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Recent Advances and Prospects in Manganese‐Catalyzed C−H Activation

Anusree,

Devi,

Anilkumar

2024

Adv Synth Catal

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Six-membered ring systems: pyridines and benzo derivatives

Badenock¹

2023

Progress in Heterocyclic Chemistry

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Morpholine Radical in the Electrochemical Reaction with Quinoline N-Oxide

Dolengovski,

Gryaznova,

Sinyashin

et al. 2023

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An electrochemical reaction between quinoline N-oxides and morpholine was developed by using Cu(OAc)2 as a catalyst, generating products of 4-aminoquinoline N-oxides in CH2Cl2 or 2-aminoquinoline N-oxides in CH3CN in good yields. With an increase in the amount of electricity passed, the product deoxygenates with the formation of aminoquinolines. The advantages of the reaction are mild conditions, room temperature, the use of morpholine rather than its derivatives, and the ability to control the process when the electrolysis conditions change. Bisubstituted quinoline has also been obtained. The redox properties of both individual participants of C–H/N–H cross-coupling and multicomponent systems were established by voltammetry and EPR methods. For the first time, the EPR spectrum of the morpholine radical was recorded at room temperature, and its magnetic resonance parameters were determined in CH2Cl2. Mechanisms for the catalytic reaction have been proposed. This is a simple and easy-to-perform method for introducing a morpholine substituent, important in medicinal chemistry and other fields, by C–H/N–H cross-coupling.

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Copper/manganese oxide catalyzed regioselective amination of quinoline N-oxides: An example of synergistic cooperative catalysis

Cited by 3 publications

References 35 publications

Recent Advances and Prospects in Manganese‐Catalyzed C−H Activation

Recent Advances and Prospects in Manganese‐Catalyzed C−H Activation

Six-membered ring systems: pyridines and benzo derivatives

Morpholine Radical in the Electrochemical Reaction with Quinoline N-Oxide

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