Digitized Honors Theses (2002-2017)
Date of Award
5-2017
Document Type
Thesis
Degree Name
BS
Department
Chemistry
Faculty Mentor
Larry Yet, Ph.D.
Advisor(s)
David Forbes,Ph.D., James Davis, Jr., Ph.D.
Abstract
The metal-catalyzed cross-coupling reactions in synthetic organic chemistry have sky-rocketed exponentially since the monumental discoveries from the laboratories of Professors Akira Suzuki, Richard Heck, and Ei-ichi Negishi, recipients of the 2010 Nobel Prize in Chemistry. Cross-coupling reactions are regularly employed in the syntheses of various carbon-carbon and carbon-heteroatom bonds such as C-N, C-P, C-O, and C-S and in the preparation of carbocyclic and heterocyclic single ring or fused ring systems. In the palladium-catalyzed cross-coupling reactions, there are several key mechanistic steps during this process where the final reductive elimination is the rate-determining step and "ligands" can facilitate this key reductive elimination step in a catalytic fashion. Successful "ligands" can include electron-donating bulky phosphine containing compounds. Imidazo[x,y-a]pyridine structures are called "privileged structures" in medicinal chemistry and our group is interested in utilizing "privileged structures" from the medicinal chemistry literature as viable "ligands" in future cross-coupling reactions. The overall successful syntheses of various phosphorus imidazo[x,y-a]pyridine ligands follows a general synthetic route ofhalogenation of the core imidazo[x,y-a]pyridine scaffold with subsequent palladium-catalyzed cross-coupling reactions of the halogenated intermediate with dialkyl- and diphenylphosphines. The core imidazo[x.y-a]pyridine intermediates could be synthesized from precursors such as imidazo[ 1,5-a ]pyridine, imidazo[ 1,2-a ]pyridine, 2-aminopyridines, and arylacetylenes.
Recommended Citation
Roberts, Kaitlyn Elise, "Synthesis of Phosphorus Imidazo [x,y-a] Pyridine Ligands" (2017). Digitized Honors Theses (2002-2017). 1.
https://jagworks.southalabama.edu/honors_theses-boundprint/1