The Development and Mechanistic Investigation of Ni(0)/Silane Catalytic Systems for the Transformation of Alkenes

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dc.contributor.advisorCook, Amanda
dc.contributor.authorKawamura, Kiana
dc.date.accessioned2022-10-04T20:46:15Z
dc.date.issued2022-10-04
dc.description.abstractThe transformation of alkenes plays an important role in chemical transformations from a scale that spans fine chemical, natural product synthesis up to the industrial scale synthesis of materials. The development of new catalytic methods that broaden substrate scopes, provide mechanistic understanding, and contribute fundamental knowledge of reactivity is critical to continually improve chemical synthesis. The focus of this thesis is centered on investigating the feasibility of using molecular silanes as mild and modular hydride sources in Ni catalysis. Reaction development of a Ni(0)/silane catalytic system for alkene isomerization, mechanistic elucidation of the catalytic system, and preliminary application of this knowledge toward the rational design of more complex tandem catalytic systems for the remote functionalization of alkenes are reported. Chapter I motivates the development of Ni-based catalytic systems for the transformation of alkenes and explains our inspiration and approach to developing the catalytic system described in Chapter II. Chapter II outlines the development of a Ni(0)/silane catalytic system for alkene isomerization. The substrate scope and initial mechanistic information is included. Chapter III describes the deeper mechanistic investigation of the Ni(0)/silane catalytic system developed in Chapter II. The focus of this chapter is on elucidating the impact of substrate structure on the observed mechanism. Chapter IV builds on the mechanistic work explored in Chapters II and III by expanding the library of ligands used, showing the feasibility of using steric modulation to enhance catalytic activity. Chapter IV also presents preliminary work toward developing an in situ approach to make this Ni(0)/silane catalytic system more practical and easily modified for different synthetic goals. Chapter V outlines our approach and initial efforts to develop a catalytic system for the remote hydroboration of alkenes. This dissertation includes previously published and unpublished coauthored material.en_US
dc.description.embargo2024-08-09
dc.identifier.urihttps://hdl.handle.net/1794/27655
dc.language.isoen_US
dc.publisherUniversity of Oregon
dc.rightsAll Rights Reserved.
dc.subjectalkenesen_US
dc.subjectcatalysisen_US
dc.subjectnickelen_US
dc.subjectorganometallicen_US
dc.titleThe Development and Mechanistic Investigation of Ni(0)/Silane Catalytic Systems for the Transformation of Alkenes
dc.typeElectronic Thesis or Dissertation
thesis.degree.disciplineDepartment of Chemistry and Biochemistry
thesis.degree.grantorUniversity of Oregon
thesis.degree.leveldoctoral
thesis.degree.namePh.D.

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