Supervisors info:
Γεώργιος Βουγιουκαλάκης, Αναπληρωτής Καθηγητής, Τμήμα Χημείας, Εθνικό και Καποδιστριακό Πανεπιστήμιο Αθηνών
Summary:
Propargylamines comprise a group of organic compounds with interesting properties and applications. These compounds can lead to a variety of different organic molecules, following their appropriate derivatization, while their bioactive properties are also being studied, particularly for the treatment of neurodegenerative diseases. Due to their inherent value, the development of novel methods for the synthesis of propargylamines is a goal of many research groups. More specifically, the subclass of tetrasubstituted propargylamines can be synthetically approached by the multicomponent reaction between ketones, amines, and terminal alkynes, also known as the KA2 reaction, using metal-based catalysts. Despite the usefulness of this transformation, the KA2 coupling has remained relatively unexplored, in relation to other reactions that achieve the synthesis of propargylamines. In the present study, the development of a novel catalytic system for the synthesis of tetrasubstituted propargylamines by the KA2 reaction is described. This system is based on the catalytic activity of a copper(I) complex with a N-heterocyclic carbene ligand. During the development of the catalytic protocol, emphasis was placed on the efficient use of low catalyst loading, low temperature, and short reaction time, in the context of the KA2 reaction, as well as on the introduction and utilization of structurally diverse substrates.
Keywords:
Organometallic catalysis, N-heterocyclic carbene complexes of copper(I), multicomponent reactions, propargylamines, tetrasubstituted carbon centers.
