Supervisors info:
Γεώργιος Βουγιουκαλάκης, Επίκουρος Καθηγητής, Τμήμα Χημείας, Εθνικό και Καποδιστριακό Πανεπιστήμιο Αθηνών
Summary:
Propargylamines, comprise a highly interesting family of compounds, which can be easily modified, thus leading to a variety of other compounds. Moreover, they possess remarkable bioactivity. As a result, their straightforward synthesis is the goal of many research groups, which has led to the development of multiple catalytic protocols. In this context, the sub-category of tetrasubstituted propargylamines can be approached synthetically using the multicomponent KA2 coupling (Ketone-Amine-Alkyne). Nevertheless, this reaction remains relatively unexplored, both in terms of the number of reported catalytic protocols and its precise mechanism. In the present study, the development of a novel catalytic system for the KA2 reaction is described. This system is based on manganese bromide, which is an economic, widely available and low-toxicity metal salt. During the development of the protocol, emphasis was given on the user-friendly characteristics of this system and its compliance with the principles of “Green Chemistry”. Noteworthy elements of our strategy are the absence of solvent, the particularly low catalyst loading, the applicability on a plethora of different substrates, as well as evidence of activity even under a non-inert atmosphere. Additionally, evidence for the introduction of aromatic amines into the KA2 reaction is provided for the first time.
Keywords:
Organic Chemistry, Sustainable Catalysis, multicomponent reactions, C-H activation, manganese acetylides, propargylamines, tetrasubstituted carbon centers.
