Chromium- and cobalt-catalyzed cross-coupling and amination reactions and synthesis and reactivity of Pyrido[3,2-f][1,7]naphthyridines

Fernandez, Sarah (2016): Chromium- and cobalt-catalyzed cross-coupling and amination reactions and synthesis and reactivity of Pyrido[3,2-f][1,7]naphthyridines. Dissertation, LMU München: Faculty of Chemistry and Pharmacy

Abstract

This work focused on the search for alternative metals to replace palladium- and nickel-catalysts by the development of new cobalt(II)- and chromium(II)-catalyzed cross-coupling methodologies. Furthermore, an effective strategy to obtain highly functionalized structural heterocyclic motifs involves the use of polyhalogenated starting materials that can be subsequently functionalized. For this purpose, the use of CrCl2 in highly regioselective cross-coupling reactions of dichlorinated heteroaromatics was demonstrated. Attention was also paid to the effective purging of chromium salts from the desired product by demonstrating the use of various solid supports for the removal of remaining metal traces. Besides the C-C bond formation, this work focused on the replacement of the cost-intensive palladium salt associated with sensitive phosphine ligands in the Buchwald- Hartwig amination reaction. Therefore, the chromium(II)-chloride catalyzed amination of N- heterocyclic chlorides with a range of magnesium amides was developed. Besides, particular attention was paid to the synthesis and functionalization of unexplored annelated six-membered N-heterocycles having potential use in medicinal and/or material applications: pyrido[3,2-f][1,7]naphthyrdine.

• Item Type: Theses (Dissertation, LMU Munich)
• Keywords: cross-coupling, amination, chromium, cobalt, naphthyridine
• Subjects: 500 Natural sciences and mathematics; 500 Natural sciences and mathematics > 540 Chemistry and allied sciences
• Faculties: Faculty of Chemistry and Pharmacy
• Language: English
• Date of oral examination: 13. May 2016
• 1. Referee: Knochel, Paul
• Signature of the printed copy: 0001/UMC 23833