Design of Ferrocene and Proline Functionalized Pyrrolinium Salts as Synthons for Cyclic (alkyl)(amino)carbenes [CAACs]

Mondal, Ankita (2025) Design of Ferrocene and Proline Functionalized Pyrrolinium Salts as Synthons for Cyclic (alkyl)(amino)carbenes [CAACs]. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS Dissertation of Ankita Mondal (23MP007)) 23MP007_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (2MB)

Abstract

Cyclic (alkyl)(amino)carbenes (CAACs) are a unique class of stable carbenes known for their exceptional σ-donating and π-accepting abilities, distinguishing them from traditional Nheterocyclic carbenes (NHCs). In this project, we explore the synthesis and characterization of donor-functionalized Ferrocene and proline based CAAC ligands. The incorporation of donor groups aims to modulate the electronic and steric properties of CAACs, enhancing their utility in catalysis. We selected ferrocene due to its redox-switchable properties, which make it highly suitable for applications involving redox catalysis. Its reversible oxidation states, stability, and tunable electronic characteristics allow for dynamic control in redoxsensitive processes. Separately, proline was chosen for its utility in asymmetric catalysis. As a simple, naturally occurring chiral molecule, proline has proven effective in promoting some assymetric catalysis for enantioselective transformations. Its catalytic efficiency and ability to induce stereocontrol make it an ideal candidate for developing asymmetric methodologies. In this project, we synthesized three types of ligand systems: Ferrocene-based N-sided pyrrolinium salt Ferrocene-based C-sided pyrrolinium salt Proline-based N-sided pyrrolinium salt Upon deprotonation of the C-sided ferrocene pyrrolinium salt, we successfully generated a free carbene species.

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