New Approaches to Nitrogen-Containing Compounds - Organocatalyzed Amination and Photoinduced Aminoalkylation

dc.contributor.advisorComito, Robert J.
dc.contributor.committeeMemberMay, Jeremy A.
dc.contributor.committeeMemberZastrow, Melissa L.
dc.contributor.committeeMemberLee, T. Randall
dc.contributor.committeeMemberKarim, Alamgir
dc.creatorTang, Zilu
dc.creator.orcid0000-0002-6504-8908
dc.date.accessioned2023-06-14T17:29:57Z
dc.date.createdMay 2023
dc.date.issued2023-04-25
dc.date.updated2023-06-14T17:29:58Z
dc.description.abstractNitrogen-containing compounds, including basic amines and N-aryl azoles, are essential building blocks to construct functional molecules, including transition-metal catalysis ligands and pharmaceutical compounds. Although the methodology for these compounds has been investigated for a few decades, significant limitations and drawbacks remain. Therefore, new synthetic pathways toward nitrogen-containing compounds are still in high demand. Two new approaches to nitrogen-containing compounds have been developed. Firstly, we achieved the transition-metal-free condensation between phenols and sulfones. The reaction furnished the N-aryl products in high yield through a nucleophilic aromatic substitution process. A plausible mechanism was proposed with the characterization of key intermediates. Secondly, we reported an intermolecular imine alkylation involving C-H activation and triplet photochemistry. The transformation was transition-metal-free, with no protecting or leaving group, under mild conditions, and delivered the primary amines directly. The scope of this reaction was broad, and most substrates gave a high yield. Besides that, the protocol was successfully operated on the inactive sp3 C-H bonds and tolerated oxidable, coordinating, and protic functional groups. Moreover, a detailed triplet excited-state mechanism for this reaction was proposed and fully characterized by mechanistic experiments.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/10657/14534
dc.language.isoeng
dc.rightsThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).
dc.subjectAmine
dc.subjectAzole
dc.subjectOrganocatalysis
dc.subjectPhotochemical
dc.titleNew Approaches to Nitrogen-Containing Compounds - Organocatalyzed Amination and Photoinduced Aminoalkylation
dc.type.dcmiText
dc.type.genreThesis
dcterms.accessRightsThe full text of this item is not available at this time because the student has placed this item under an embargo for a period of time. The Libraries are not authorized to provide a copy of this work during the embargo period.
local.embargo.lift2025-05-01
local.embargo.terms2025-05-01
thesis.degree.collegeCollege of Natural Sciences and Mathematics
thesis.degree.departmentChemistry, Department of
thesis.degree.disciplineChemistry
thesis.degree.grantorUniversity of Houston
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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