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Manganese‐Catalyzed Multicomponent Synthesis of Tetrasubstituted Propargylamines: System Development and Theoretical Study

Stavros P. Neofotistos, Nikolaos V. Tzouras, Martin Pauze, Enrique Gómez‐Bengoa, Georgios C. Vougioukalakis

2020Advanced Synthesis & Catalysis30 citationsDOIOpen Access PDF

Abstract

Abstract Herein, we report a catalytic system based on the earth‐abundant manganese for the ketone, amine, alkyne (KA 2 ) reaction. The efficiency of manganese manifests at relatively high temperatures, combined with sustainable reaction conditions, and provides a tool for accessing propargylamines from structurally diverse starting materials, including synthetically relevant and bioactive molecules. Our efforts were also aimed at shedding light on the catalytic mode of action of manganese in this transformation, in order to explain its temperature‐related behavior. The use of computational methods reveals mechanistic aspects of this reaction indicating important points regarding the reactivity of both manganese and ketones. magnified image

Topics & Concepts

ManganeseChemistryCatalysisCombinatorial chemistryAmine gas treatingReactivity (psychology)AlkyneKetoneMoleculeOrganic chemistryAlternative medicinePathologyMedicineCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods
Manganese‐Catalyzed Multicomponent Synthesis of Tetrasubstituted Propargylamines: System Development and Theoretical Study | Litcius