{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/113151"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/113151","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Development of three-component alkene and 1,3-diene carbofunctionalization reactions","abstract":"Given the prevalence of nitrogen-containing molecules in pharmaceuticals and agrochemicals, the development of efficient amination reactions is an essential research effort within the broad confines of organic method development. The ever-increasing complexity of the molecular structures used to treat human illness demands that novel transformations utilize mild reaction conditions, tolerate preexisting functionality, and rapidly produce structural complexity from accessible functionality. Furthermore, given the potential of novel strategic advances to productively alter the logic of complex molecule synthesis, the establishment of unintuitive retrosynthetic disconnections to achieve orthogonal means of access to desirable structures is of intense interest. In accord with these demands, we have developed a three-component alkene carboamination reaction. This system offers access to complex amine products from simple starting materials and proceeds under mild reaction conditions. Critically, this transformation combines disconnected carbon, nitrogen, and alkene moieties as independent reaction components, thus enabling the modular assembly of structurally diverse amines from a single reaction system. The discovery, development, and assessment of this system is detailed in the first chapter of this document. In the second chapter, the expansion of this system to achieve a general alkene carbofunctionalization system is explored, revealing that this strategy is capable of delivering carboesterification, carboetherification, and carboarylation products in addition to complex amines. The final chapter of this dissertation explores the development of a novel strategy for accessing allylic amines via a three-component 1,3-diene carboamination reaction. Utilizing many of the principles uncovered while developing the alkene functionalization reactions of the prior chapters, this system facilitates modular access to allylic amines that does not require the manipulation of preexisting allylic functionality. The discovery, development, and assessment of this novel system with respect to several classes of 1,3-dienes is presented.","abstract_html":"Given the prevalence of nitrogen-containing molecules in pharmaceuticals and agrochemicals, the development of efficient amination reactions is an essential research effort within the broad confines of organic method development. The ever-increasing complexity of the molecular structures used to treat human illness demands that novel transformations utilize mild reaction conditions, tolerate preexisting functionality, and rapidly produce structural complexity from accessible functionality. Furthermore, given the potential of novel strategic advances to productively alter the logic of complex molecule synthesis, the establishment of unintuitive retrosynthetic disconnections to achieve orthogonal means of access to desirable structures is of intense interest. In accord with these demands, we have developed a three-component alkene carboamination reaction. This system offers access to complex amine products from simple starting materials and proceeds under mild reaction conditions. Critically, this transformation combines disconnected carbon, nitrogen, and alkene moieties as independent reaction components, thus enabling the modular assembly of structurally diverse amines from a single reaction system. The discovery, development, and assessment of this system is detailed in the first chapter of this document. In the second chapter, the expansion of this system to achieve a general alkene carbofunctionalization system is explored, revealing that this strategy is capable of delivering carboesterification, carboetherification, and carboarylation products in addition to complex amines. The final chapter of this dissertation explores the development of a novel strategy for accessing allylic amines via a three-component 1,3-diene carboamination reaction. Utilizing many of the principles uncovered while developing the alkene functionalization reactions of the prior chapters, this system facilitates modular access to allylic amines that does not require the manipulation of preexisting allylic functionality. The discovery, development, and assessment of this novel system with respect to several classes of 1,3-dienes is presented.","abstract_has_math":false,"creators":["Buchanan, Travis Lamonte"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Hull, Kami L","Chan, Jefferson","Girolami, Gregory S","Zimmerman, Steven C"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-01-12T22:35:04Z","date_published":"2022-01-12T22:35:04Z","updated_at":"2026-07-22T22:24:53Z","subjects":["alkene difunctionalization","copper","catalysis","carboamination"],"languages":["en"],"rights":["Copyright 2021 Travis Buchanan"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/2142/113151","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Hull, Kami L","Chan, Jefferson","Girolami, Gregory S","Zimmerman, Steven C"]},{"key":"dc:creator","label":"Author","values":["Buchanan, Travis Lamonte"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2022-01-12T22:35:04Z","2024-01-12T22:35:30Z","2021-07-09","2021-08"]},{"key":"dc:type","label":"Dc Type","values":["text","Thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["alkene difunctionalization","copper","catalysis","carboamination"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 2021 Travis Buchanan"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/113151"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Given the prevalence of nitrogen-containing molecules in pharmaceuticals and agrochemicals, the development of efficient amination reactions is an essential research effort within the broad confines of organic method development. The ever-increasing complexity of the molecular structures used to treat human illness demands that novel transformations utilize mild reaction conditions, tolerate preexisting functionality, and rapidly produce structural complexity from accessible functionality. Furthermore, given the potential of novel strategic advances to productively alter the logic of complex molecule synthesis, the establishment of unintuitive retrosynthetic disconnections to achieve orthogonal means of access to desirable structures is of intense interest. In accord with these demands, we have developed a three-component alkene carboamination reaction. This system offers access to complex amine products from simple starting materials and proceeds under mild reaction conditions. Critically, this transformation combines disconnected carbon, nitrogen, and alkene moieties as independent reaction components, thus enabling the modular assembly of structurally diverse amines from a single reaction system. The discovery, development, and assessment of this system is detailed in the first chapter of this document. In the second chapter, the expansion of this system to achieve a general alkene carbofunctionalization system is explored, revealing that this strategy is capable of delivering carboesterification, carboetherification, and carboarylation products in addition to complex amines. The final chapter of this dissertation explores the development of a novel strategy for accessing allylic amines via a three-component 1,3-diene carboamination reaction. Utilizing many of the principles uncovered while developing the alkene functionalization reactions of the prior chapters, this system facilitates modular access to allylic amines that does not require the manipulation of preexisting allylic functionality. The discovery, development, and assessment of this novel system with respect to several classes of 1,3-dienes is presented.","Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2023-08-01","The student, Travis Buchanan, accepted the attached license on 2021-07-07 at 16:52.","The student, Travis Buchanan, submitted this Dissertation for approval on 2021-07-07 at 17:03.","This Dissertation was approved for publication on 2021-07-09 at 17:22.","DSpace SAF Submission Ingestion Package generated from Vireo submission #16790 on 2022-01-12 at 12:53:50","Made available in DSpace on 2022-01-12T22:35:04Z (GMT). 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The ever-increasing complexity of the molecular structures used to treat human illness demands that novel transformations utilize mild reaction conditions, tolerate preexisting functionality, and rapidly produce structural complexity from accessible functionality. Furthermore, given the potential of novel strategic advances to productively alter the logic of complex molecule synthesis, the establishment of unintuitive retrosynthetic disconnections to achieve orthogonal means of access to desirable structures is of intense interest. In accord with these demands, we have developed a three-component alkene carboamination reaction. This system offers access to complex amine products from simple starting materials and proceeds under mild reaction conditions. Critically, this transformation combines disconnected carbon, nitrogen, and alkene moieties as independent reaction components, thus enabling the modular assembly of structurally diverse amines from a single reaction system. The discovery, development, and assessment of this system is detailed in the first chapter of this document. In the second chapter, the expansion of this system to achieve a general alkene carbofunctionalization system is explored, revealing that this strategy is capable of delivering carboesterification, carboetherification, and carboarylation products in addition to complex amines. The final chapter of this dissertation explores the development of a novel strategy for accessing allylic amines via a three-component 1,3-diene carboamination reaction. Utilizing many of the principles uncovered while developing the alkene functionalization reactions of the prior chapters, this system facilitates modular access to allylic amines that does not require the manipulation of preexisting allylic functionality. The discovery, development, and assessment of this novel system with respect to several classes of 1,3-dienes is presented.","Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2023-08-01","The student, Travis Buchanan, accepted the attached license on 2021-07-07 at 16:52.","The student, Travis Buchanan, submitted this Dissertation for approval on 2021-07-07 at 17:03.","This Dissertation was approved for publication on 2021-07-09 at 17:22.","DSpace SAF Submission Ingestion Package generated from Vireo submission #16790 on 2022-01-12 at 12:53:50","Made available in DSpace on 2022-01-12T22:35:04Z (GMT). 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