Repository logo
 

Phosphorus ligand-coupling reactions for the functionalization of pyridine and other azines

Simple item page
dc.contributor.authorNottingham, Kyle G., author
dc.contributor.authorMcNally, Andrew, advisor
dc.contributor.authorPaton, Robert, committee member
dc.contributor.authorHenry, Chuck, committee member
dc.contributor.authorCohen, Robert, committee member
dc.date.accessioned2021-09-06T10:26:10Z
dc.date.available2023-09-03T10:26:10Z
dc.date.issued2021
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.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2020-
dc.rightsCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.
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.embargo.terms2023-09-03
dcterms.rights.dplaThis Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

Files

Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
Nottingham_colostate_0053A_16707.pdf
Size:
19.93 MB
Format:
Adobe Portable Document Format
Download

Collections

2020-
Theses and Dissertations