{"id":{"repo_id":"houston","oai_identifier":"oai:uh-ir.tdl.org:10657/17741"},"canonical_url":"https://search.dev.ndltd.org/etd/houston/oai:uh-ir.tdl.org:10657/17741","repository":{"repo_id":"houston","name":"University of Houston","base_url":"https://uh-ir.tdl.org/server/oai/request"},"display":{"title":"Carbon-Carbon Bonds Formed by Lewis Acid Catalysis or Photoactivation","abstract":"Methods to generate C¬–C bonds are of great interest to synthetic organic chemists. Ideally, these reactions will be simple, robust, and catalytic. Herein is described the synthesis of tertiary and all-carbon quaternary centers from propargylic alcohols, organoboronates, and Lewis acids. Lewis acids can also be used to facilitate a mild Friedel-Crafts reaction between electron-rich aromatics and allylic or benzylic alcohols. Moreover, these methods can be applied to the synthesis of natural products. Finally, photoactivation of tosylhydrazones can allow for C–C bond formation when paired with organoboronates. This reaction was probed and the mechanism of photoactivation was elucidated.","abstract_html":"Methods to generate C¬–C bonds are of great interest to synthetic organic chemists. Ideally, these reactions will be simple, robust, and catalytic. Herein is described the synthesis of tertiary and all-carbon quaternary centers from propargylic alcohols, organoboronates, and Lewis acids. Lewis acids can also be used to facilitate a mild Friedel-Crafts reaction between electron-rich aromatics and allylic or benzylic alcohols. Moreover, these methods can be applied to the synthesis of natural products. Finally, photoactivation of tosylhydrazones can allow for C–C bond formation when paired with organoboronates. This reaction was probed and the mechanism of photoactivation was elucidated.","abstract_has_math":false,"creators":["Donald, Clayton Paul"],"institution":"University of Houston","degree_name":"Doctor of Philosophy","degree_level":"Doctoral","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":["May, Jeremy A"],"committee_chairs":[],"committee_members":["Gilbertson, Scott R","Daugulis, Olafs","Cuny, Gregory","Teets, Thomas S"],"year":2024,"date_issued":"2024-04-04","date_published":"2024-04-04","updated_at":"2026-07-24T02:31:59Z","subjects":["Synthesis","Catalysis","Photoactivation","Carbon-Carbon Bonds"],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10657/17741","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["May, Jeremy A"]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Gilbertson, Scott R","Daugulis, Olafs","Cuny, Gregory","Teets, Thomas S"]},{"key":"dc:creator","label":"Author","values":["Donald, Clayton Paul"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2024-07-26T23:00:22Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2024-07-26T23:00:22Z"]},{"key":"dc:date.issued","label":"Date","values":["2024-04-04"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Doctoral"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Houston"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Synthesis","Catalysis","Photoactivation","Carbon-Carbon Bonds"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/10657/17741"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Methods to generate C¬–C bonds are of great interest to synthetic organic chemists. Ideally, these reactions will be simple, robust, and catalytic. Herein is described the synthesis of tertiary and all-carbon quaternary centers from propargylic alcohols, organoboronates, and Lewis acids. Lewis acids can also be used to facilitate a mild Friedel-Crafts reaction between electron-rich aromatics and allylic or benzylic alcohols. Moreover, these methods can be applied to the synthesis of natural products. Finally, photoactivation of tosylhydrazones can allow for C–C bond formation when paired with organoboronates. This reaction was probed and the mechanism of photoactivation was elucidated."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Carbon-Carbon Bonds Formed by Lewis Acid Catalysis or Photoactivation"]}]}],"canonical_facts":{"dc:contributor.advisor":["May, Jeremy A"],"dc:contributor.committeemember":["Gilbertson, Scott R","Daugulis, Olafs","Cuny, Gregory","Teets, Thomas S"],"dc:creator":["Donald, Clayton Paul"],"dc:date.accessioned":["2024-07-26T23:00:22Z"],"dc:date.available":["2024-07-26T23:00:22Z"],"dc:date.issued":["2024-04-04"],"dc:description.abstract":["Methods to generate C¬–C bonds are of great interest to synthetic organic chemists. Ideally, these reactions will be simple, robust, and catalytic. Herein is described the synthesis of tertiary and all-carbon quaternary centers from propargylic alcohols, organoboronates, and Lewis acids. Lewis acids can also be used to facilitate a mild Friedel-Crafts reaction between electron-rich aromatics and allylic or benzylic alcohols. Moreover, these methods can be applied to the synthesis of natural products. Finally, photoactivation of tosylhydrazones can allow for C–C bond formation when paired with organoboronates. This reaction was probed and the mechanism of photoactivation was elucidated."],"dc:format.mimetype":["application/pdf"],"dc:identifier.uri":["https://hdl.handle.net/10657/17741"],"dc:language.iso":["en"],"dc:subject":["Synthesis","Catalysis","Photoactivation","Carbon-Carbon Bonds"],"dc:title":["Carbon-Carbon Bonds Formed by Lewis Acid Catalysis or Photoactivation"],"dc:type":["Thesis"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Doctoral"],"thesis:degree_name":["Doctor of Philosophy"],"thesis:institution_name":["University of Houston"]},"updated_at":"2026-07-24T02:31:59Z"}