{"id":{"repo_id":"buffalo","oai_identifier":"oai:ubir.buffalo.edu:10477/80901"},"canonical_url":"https://search.dev.ndltd.org/etd/buffalo/oai:ubir.buffalo.edu:10477/80901","repository":{"repo_id":"buffalo","name":"Buffalo","base_url":"https://ubir.buffalo.edu/oai/request"},"display":{"title":"Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N-Sulfonyl Aldimines and Oxidative Coupling of Alkyltrifluoroborates with Alkenols, Alkenoic Acids, and Alkenylamides","abstract":"Ph.D.","abstract_html":"Ph.D.","abstract_has_math":false,"creators":["Shikora, Jonathan"],"institution":"State University of New York at Buffalo","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Chemler, Sherry","Chemistry"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2019,"date_issued":"2019-10-29T16:48:00Z","date_published":"2019-10-29T16:48:00Z","updated_at":"2026-07-27T19:05:25Z","subjects":["organic chemistry"],"languages":["eng"],"rights":["Users of works found in University at Buffalo Institutional Repository (UBIR) are responsible for identifying and contacting the copyright owner for permission to reuse. University at Buffalo Libraries do not manage rights for copyright-protected works and cannot assist with permissions.","Copyright retained by author."],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10477/80901","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Chemler, Sherry","Chemistry"]},{"key":"dc:creator","label":"Author","values":["Shikora, Jonathan"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2019-10-29T16:48:00Z","2019","2019-08-06 16:58:32"]},{"key":"dc:publisher","label":"Institution","values":["State University of New York at Buffalo"]},{"key":"dc:type","label":"Dc Type","values":["Text","Dissertation"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["organic chemistry"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Users of works found in University at Buffalo Institutional Repository (UBIR) are responsible for identifying and contacting the copyright owner for permission to reuse. University at Buffalo Libraries do not manage rights for copyright-protected works and cannot assist with permissions.","Copyright retained by author."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/10477/80901"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Ph.D.","Copper(II) triflate has long been known as a useful catalyst for organic transformations. Not only is it a powerful Lewis acid, but it can also be used in one and two electron redox transfer processes. The research presented here aims to describe the use of copper(II) triflate, in conjunction with an organic ligand, as the catalyst used in the highly enantioselective aza-Friedel-Crafts reaction between phenols and aldimines and the oxidative coupling/cyclization of alkyl radicals derived from potassium alkyltrifluoroborate salts to alkenoic acids, alkenols, and alkenylamides to form saturated oxygen and nitrogen containing heterocycles. In the aza-Friedel-Crafts reaction, enantioselectivies up to 99% were achieved of the chiral benzylamine products and the synthetic utility of the products were demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist and a chiral tetrahydroquinoline. For the oxidative coupling/cyclization reaction, 5-, 6-, and 7-membered oxygen and nitrogen containing rings were formed by coupling alkyltrifluoroborates with heteroatom-tethered alkenes in a net alkene difunctionalization reaction. The reactivity was consistent with a mixed polar/radical mechanism involving the addition of alkyl radicals to styrenes followed by [Cu(III)]-facilitated C-O or C-N bond formation."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N-Sulfonyl Aldimines and Oxidative Coupling of Alkyltrifluoroborates with Alkenols, Alkenoic Acids, and Alkenylamides"]}]}],"canonical_facts":{"dc:contributor":["Chemler, Sherry","Chemistry"],"dc:creator":["Shikora, Jonathan"],"dc:date":["2019-10-29T16:48:00Z","2019","2019-08-06 16:58:32"],"dc:description":["Ph.D.","Copper(II) triflate has long been known as a useful catalyst for organic transformations. Not only is it a powerful Lewis acid, but it can also be used in one and two electron redox transfer processes. The research presented here aims to describe the use of copper(II) triflate, in conjunction with an organic ligand, as the catalyst used in the highly enantioselective aza-Friedel-Crafts reaction between phenols and aldimines and the oxidative coupling/cyclization of alkyl radicals derived from potassium alkyltrifluoroborate salts to alkenoic acids, alkenols, and alkenylamides to form saturated oxygen and nitrogen containing heterocycles. In the aza-Friedel-Crafts reaction, enantioselectivies up to 99% were achieved of the chiral benzylamine products and the synthetic utility of the products were demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist and a chiral tetrahydroquinoline. For the oxidative coupling/cyclization reaction, 5-, 6-, and 7-membered oxygen and nitrogen containing rings were formed by coupling alkyltrifluoroborates with heteroatom-tethered alkenes in a net alkene difunctionalization reaction. The reactivity was consistent with a mixed polar/radical mechanism involving the addition of alkyl radicals to styrenes followed by [Cu(III)]-facilitated C-O or C-N bond formation."],"dc:format":["application/pdf"],"dc:identifier":["http://hdl.handle.net/10477/80901"],"dc:language":["eng"],"dc:publisher":["State University of New York at Buffalo"],"dc:rights":["Users of works found in University at Buffalo Institutional Repository (UBIR) are responsible for identifying and contacting the copyright owner for permission to reuse. University at Buffalo Libraries do not manage rights for copyright-protected works and cannot assist with permissions.","Copyright retained by author."],"dc:subject":["organic chemistry"],"dc:title":["Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N-Sulfonyl Aldimines and Oxidative Coupling of Alkyltrifluoroborates with Alkenols, Alkenoic Acids, and Alkenylamides"],"dc:type":["Text","Dissertation"]},"updated_at":"2026-07-27T19:05:25Z"}