Unit:
Κατεύθυνση Οργανική ΧημείαLibrary of the School of Science
Author:
Liori Angeliki-Spyridoula
Supervisors info:
Γεώργιος Βουγιουκαλάκης, Επίκουρος Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Original Title:
Ενεργοποίηση δεσμών C-H καταλυόμενη από χαλκό και Ν-ετεροκυκλικά καρβένια με εφαρμογή στην αντίδραση Sonogashira και την καρβοξυλίωση τελικών αλκινίων
Translated title:
C-H Bond Activation catalyzed by copper and N-heterocyclic carbenes-Application to Sonogashira reaction and to carboxylation reaction of terminal alkynes
Summary:
The omnipresence of C-H bonds in organic compounds renders them highly attractive targets for the installation of functional groups towards the construction of valuable molecular scaffolds. Consequently, C-H activation has evolved beyond scientific curiosity and has extended from being a concept of fundamental interest to constituting an important tool of organic synthesis. C-H activation catalyzed by cheap, abundant and non-toxic copper has lately attracted researchers’ interest. At the same time, N-heterocyclic carbenes (NHCs) are powerful tools with many applications, specifically in homogeneous catalysis. In the present thesis, the concept of N-heterocyclic carbenes is being introduced in the first chapter, followed by an introduction in C-H activation (second chapter). In the third and fourth chapters, the carboxylation of terminal alkynes and the Sonogashira coupling are being reviewed.
The research goals of this thesis, discussed in chapters fifth through eighth, were:
• The synthesis of a family of saturated symmetrical N-heterocyclic carbene ligands.
• The synthesis of a series of sustainable, homogeneous Cu-based catalytic systems by employing the corresponding N-heterocyclic carbene ligands.
• The catalytic transformation of carbon dioxide into useful chemical structures (CO2 monetization), specifically through carboxylation of terminal alkynes.
• The Sonogashira cross-coupling reaction between terminal alkynes and arylhalides, catalyzed by novel copper catalytic systems bearing N-heterocyclic carbenes under palladium-free conditions.
Finally, all experimental procedures as well as the spectroscopic data of the synthesized compounds are described in the ninth chapter.
Main subject category:
Science
Keywords:
N-heterocyclic carbenes, organic synthesis, homogeneous catalysis, transition metal complexes, copper, terminal alkynes, cross-coupling, Sonogashira reaction, carbon dioxide
Number of index pages:
12
Number of references:
181
