transition metal ligands for suzuki-miyaura cross-coupling reactions and the coordination of radionuclides - studies towards aurora kinase inhibition for pet imaging
abstract
this thesis is wide-ranging covering disparate areas of synthetic organic and metalorganic
chemistry, unified by the general use of these projects in medicinal chemistry.
two organometallic palladium complexes 2.3 and 2.4, the 2-methyl-4-phenyl-1,3-
thiazole and the 4-phenyl-1,3-thiazol-4-ylamine ligand respectively were synthesized
and characterized using nmr, mass spectrometry, ir, and x-ray crystallography. these
catalysts were tested with various substrates to understand the influence of these catalysts
on substrates with electron-withdrawing groups or electron-donating groups in the suzuki-
miyaura cross-coupling reaction. several aryl halides and different boronic acid pairs were
studied yielding a conversion rate between 27-97 % when 5 mol % of each palladium
catalyst was used at 60 oc for 8 hours. the relative rate of electron poor aryl halides was
faster than electron rich aryl halides with catalyst 2.4 (amine substituted catalyst) showing
preference for electron-withdrawing group (ewg > edg). the relative rates of the
electron rich aryl halides were faster than the electron poor aryl halides when the catalyst
with the methyl substituted ligand (catalyst 2.3) was used and we get the opposite
preference for electron-donating group (edg > ewg). the latter behavior is unique in
suzuki-miyaura coupling reactions, which makes catalyst 2.3 a useful addition to the
family of suzuki-miyaura catalytic systems. [...]