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dc.contributor.advisorMcNally, Andrew
dc.contributor.authorNottingham, Kyle G.
dc.contributor.committeememberPaton, Robert
dc.contributor.committeememberHenry, Chuck
dc.contributor.committeememberCohen, Robert
dc.date.accessioned2021-09-06T10:26:10Z
dc.date.available2023-09-03T10:26:10Z
dc.date.issued2021
dc.description2021 Summer.
dc.descriptionIncludes bibliographical references.
dc.description.abstractPyridines and related azines are ubiquitous in pharmaceuticals, agrochemicals, and materials. The discovery and development of new purpose-built molecules is contingent on our ability to modify these motifs. Described herein are the development of methods that selectively functionalize pyridine and diazine scaffolds through phosphorus ligand-coupling. Novel phosphine reagents were designed and leveraged to construct C–C, C–O, and C–N bonds on azines from their C–H precursors. Chapter one introduces the history of phosphorus ligand-coupling and defines the reactivity explored throughout this thesis. Both seminal and contemporary examples of phosphorus ligand-coupling reactions are also discussed to provide context for this work. Chapter two focuses on a method to incorporate fluoroalkyl groups onto azines and pharmaceuticals using phosphorus ligand-coupling. This method offers a complementary alternative to widely used radical addition approaches which often produce regiomeric product mixtures on azines. Chapter three presents the investigation of a phosphorus-mediated alkenylation reaction on pyridines and quinolines. Examination of the reaction of pyridylphosphines with alkyne acceptors uncovered divergent reaction pathways from alkenylphosphonium salts. Mechanistic studies provide an explanation for the origin of selectivity obtained in these reactions. Lastly, chapter four expands upon one of these reaction pathways and describes the development of a method for the direct conversion of pyridines into pyridones and aminopyridines.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierNottingham_colostate_0053A_16707.pdf
dc.identifier.urihttps://hdl.handle.net/10217/233826
dc.languageEnglish
dc.publisherColorado State University. Libraries
dc.relation.ispartof2020- CSU Theses and Dissertations
dc.rightsCopyright of the original work is retained by the author.
dc.rights.accessEmbargo Expires: 09/03/2023
dc.subjectfluoroalkylation
dc.subjectphosphorus
dc.subjectpyridone
dc.subjectligand-coupling
dc.subjectazines
dc.subjectpyridine
dc.titlePhosphorus ligand-coupling reactions for the functionalization of pyridine and other azines
dc.typeText
dcterms.embargo.expires2023-09-03
dcterms.rights.dplaThe copyright and related rights status of this Item has not been evaluated (https://rightsstatements.org/vocab/CNE/1.0/). Please refer to the organization that has made the Item available for more information.
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)


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