Manganese-Catalyzed Multicomponent Synthesis of Tetrasubstituted Propargylamines: System Development and Theoretical Study
Ikusi/ Ireki
Data
2020-07-20Egilea
Neofotistos, Stavros P
Tzouras, Nikolaos V
Pauze, Martin Paule
Gómez Bengoa, Enrique
Vougioukalakis, Georgios C
Advanced Synthesis & Catalysis 362(18) : 3872-3885 (2020)
Laburpena
The importance of multicomponent reactions as an efficient tool in organic synthesis is widely recognized, as the need for sustainable, practical, atom- and step-economic methodologies is becoming a crucial concept in contemporary research. In this context, the synthesis of propargylamines via multicomponent protocols holds great promise, because of their biological action and their potential as synthons. Ketone-derived, tetrasubstituted propargylamines are a relatively unexplored subclass of compounds, while protocols to access them have only been described in the past decade, owing to the challenging nature of ketones as multicomponent coupling partners. Herein, we report a catalytic system based on the earth-abundant manganese for the ketone, amine, alkyne (KA2) reaction. The efficiency of manganese, combined with sustainable reaction conditions, comprise a useful new method for accessing various interesting propargylamines. Additionally, the use of computational methods reveals mechanistic aspects of this reaction, for the first time, raising important points regarding the reactivity of both manganese and ketones.