{"id":{"repo_id":"queens","oai_identifier":"oai:queensu.scholaris.ca:1974/29860"},"canonical_url":"https://search.dev.ndltd.org/etd/queens/oai:queensu.scholaris.ca:1974/29860","repository":{"repo_id":"queens","name":"Queens University","base_url":"https://qspace.library.queensu.ca/server/oai/request"},"display":{"title":"STEREOSPECIFIC SUZUKI-MIYAURA CROSS-COUPLING OF CHIRAL BENZYLIC BORONIC ESTERS AND VINYL BROMIDES","abstract":"The Suzuki-Miyaura cross-coupling reaction is a powerful method for the construction of carbon-carbon bonds in academia and industry. Despite extensive research in this area and the significance of the reaction, it is most often employed to prepare flat, Csp2-Csp2 bonds between two aryl groups. Since most bioactive compounds contain several 3-D or chiral centers, it is more desirable to make bonds between sp2-sp3 and sp3-sp3 carbon centers. However, when dealing with sp3 carbons in cross-coupling chemistry, new challenges arise such as β-hydride elimination, an undesirable side reaction. In 2009, our group reported the first example of a stereospecific coupling between chiral secondary boronic esters and aryl iodides. In this thesis, we report our investigations towards expanding the scope of our established Csp2-Csp3 coupling reaction with chiral boronic esters. By employing vinyl halides as electrophiles, we can stereospecifically prepare alkene-containing products—a useful handle for further functionalization.","abstract_html":"The Suzuki-Miyaura cross-coupling reaction is a powerful method for the construction of carbon-carbon bonds in academia and industry. Despite extensive research in this area and the significance of the reaction, it is most often employed to prepare flat, Csp2-Csp2 bonds between two aryl groups. Since most bioactive compounds contain several 3-D or chiral centers, it is more desirable to make bonds between sp2-sp3 and sp3-sp3 carbon centers. However, when dealing with sp3 carbons in cross-coupling chemistry, new challenges arise such as β-hydride elimination, an undesirable side reaction. In 2009, our group reported the first example of a stereospecific coupling between chiral secondary boronic esters and aryl iodides. In this thesis, we report our investigations towards expanding the scope of our established Csp2-Csp3 coupling reaction with chiral boronic esters. By employing vinyl halides as electrophiles, we can stereospecifically prepare alkene-containing products—a useful handle for further functionalization.","abstract_has_math":false,"creators":["Dozois, Nicole"],"institution":null,"degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":"Chemistry","school":null,"contributors":[],"advisors":["Crudden, Cathleen"],"committee_chairs":[],"committee_members":[],"year":null,"date_issued":"","date_published":null,"updated_at":"2026-07-27T20:35:37Z","subjects":["cross-coupling","catalysis","Suzuki-Miyaura"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/1974/29860","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.department","label":"Department","values":["Chemistry"]},{"key":"dc:contributor.supervisor","label":"Supervisor","values":["Crudden, Cathleen"]},{"key":"dc:creator","label":"Author","values":["Dozois, Nicole"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2021-12-23T20:32:13Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2021-12-23T20:32:13Z"]},{"key":"dc:type","label":"Dc Type","values":["thesis"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["cross-coupling","catalysis","Suzuki-Miyaura"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/1974/29860"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The Suzuki-Miyaura cross-coupling reaction is a powerful method for the construction of carbon-carbon bonds in academia and industry. Despite extensive research in this area and the significance of the reaction, it is most often employed to prepare flat, Csp2-Csp2 bonds between two aryl groups. Since most bioactive compounds contain several 3-D or chiral centers, it is more desirable to make bonds between sp2-sp3 and sp3-sp3 carbon centers. However, when dealing with sp3 carbons in cross-coupling chemistry, new challenges arise such as β-hydride elimination, an undesirable side reaction. In 2009, our group reported the first example of a stereospecific coupling between chiral secondary boronic esters and aryl iodides. In this thesis, we report our investigations towards expanding the scope of our established Csp2-Csp3 coupling reaction with chiral boronic esters. By employing vinyl halides as electrophiles, we can stereospecifically prepare alkene-containing products—a useful handle for further functionalization."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["M.Sc."]},{"key":"dc:title","label":"Title","values":["STEREOSPECIFIC SUZUKI-MIYAURA CROSS-COUPLING OF CHIRAL BENZYLIC BORONIC ESTERS AND VINYL BROMIDES"]}]}],"canonical_facts":{"dc:contributor.department":["Chemistry"],"dc:contributor.supervisor":["Crudden, Cathleen"],"dc:creator":["Dozois, Nicole"],"dc:date.accessioned":["2021-12-23T20:32:13Z"],"dc:date.available":["2021-12-23T20:32:13Z"],"dc:description.abstract":["The Suzuki-Miyaura cross-coupling reaction is a powerful method for the construction of carbon-carbon bonds in academia and industry. Despite extensive research in this area and the significance of the reaction, it is most often employed to prepare flat, Csp2-Csp2 bonds between two aryl groups. Since most bioactive compounds contain several 3-D or chiral centers, it is more desirable to make bonds between sp2-sp3 and sp3-sp3 carbon centers. However, when dealing with sp3 carbons in cross-coupling chemistry, new challenges arise such as β-hydride elimination, an undesirable side reaction. In 2009, our group reported the first example of a stereospecific coupling between chiral secondary boronic esters and aryl iodides. In this thesis, we report our investigations towards expanding the scope of our established Csp2-Csp3 coupling reaction with chiral boronic esters. By employing vinyl halides as electrophiles, we can stereospecifically prepare alkene-containing products—a useful handle for further functionalization."],"dc:description.degree":["M.Sc."],"dc:identifier.uri":["http://hdl.handle.net/1974/29860"],"dc:language.iso":["eng"],"dc:subject":["cross-coupling","catalysis","Suzuki-Miyaura"],"dc:title":["STEREOSPECIFIC SUZUKI-MIYAURA CROSS-COUPLING OF CHIRAL BENZYLIC BORONIC ESTERS AND VINYL BROMIDES"],"dc:type":["thesis"]},"updated_at":"2026-07-27T20:35:37Z"}