Development of Transformations of Pyridotriazoles and Photoinduced Palladium Hydride-enabled Reactions

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dc.contributor.advisorGevorgyan, Vladimir
dc.contributor.advisorLou, Xinchou
dc.contributor.committeeMemberSmaldone, Ronald A.
dc.contributor.committeeMemberGassensmith, Jeremiah J.
dc.contributor.committeeMemberRomiti, Filippo
dc.creatorZhang, Ziyan
dc.date.accessioned2024-03-06T15:55:43Z
dc.date.available2024-03-06T15:55:43Z
dc.date.created2023-12
dc.date.issuedDecember 2023
dc.date.submittedDecember 2023
dc.date.updated2024-03-06T15:55:44Z
dc.description.abstractThe thesis describes the development of denitrogenative transformations of pyridotriazoles and photoinduced palladium hydride-enabled reactions. A general and efficient method for arylation, X–H insertions, and cyclopropanation reactions of pyridotriazoles was developed. This protocol proceeded via pyridyl carbene intermediates, under mild, transition metal-free, and light-induced conditions. Furthermore, a Co-catalyzed transannulation reaction of pyridotriazoles with isothiocyanates and xanthate esters was developed. This method features the conversion of pyridotriazoles into two N-fused heterocycles, such as imino-thiazolopyridines and oxo- thiazolopyridine derivatives, via one-step Co(II)-catalyzed transannulation reaction proceeding though a radical mechanism. Next, three protocols enabled by visible light and palladium hydride were developed. A variety of substrates, such as diazo compounds, N-tosylhydrazones, strained molecules, acrylic acids, acrylic amides, and Baylis-Hillman adducts were found to produce hybrid palladium alkyl radical intermediates under photoinduced and palladium hydride-catalyzed conditions. These alkyl radical species subsequently participated in diverse transformations, including Heck reaction, hydroalkenylation and cascade annulation reactions.
dc.format.mimetypeapplication/pdf
dc.identifier.uri
dc.identifier.urihttps://hdl.handle.net/10735.1/9992
dc.language.isoEnglish
dc.subjectChemistry, Organic
dc.titleDevelopment of Transformations of Pyridotriazoles and Photoinduced Palladium Hydride-enabled Reactions
dc.typeThesis
dc.type.materialtext
thesis.degree.collegeSchool of Natural Sciences and Mathematics
thesis.degree.departmentChemistry
thesis.degree.grantorThe University of Texas at Dallas
thesis.degree.namePHD

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