{"id":{"repo_id":"uoit","oai_identifier":"oai:ontariotechu.scholaris.ca:10155/694"},"canonical_url":"https://search.dev.ndltd.org/etd/uoit/oai:ontariotechu.scholaris.ca:10155/694","repository":{"repo_id":"uoit","name":"Ontario Institute of Technology","base_url":"https://ontariotechu.scholaris.ca/server/oai/request"},"display":{"title":"Direct Brønsted acid-catalyzed functionalization of benzhydryl alcohols and 2-ethoxytetrahydrofuran using potassium trifluoroborate salts","abstract":"Metal-free transformations of organotrifluoroborates are advantageous since they avoid using frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving organotrifluoroborates have emerged as an alternative to metal-catalyzed protocols. However, these methods rely on generating unstable boron dihalide species thereby resulting in low functional group tolerance. A Brønsted acid-catalyzed carbon-carbon bond forming methodology involving alkenyl- and alkynyltrifluoroborates and in situ generated carbocations has been developed. In the presence of HBF4, we have shown that organotrifluoroborates react with benzhydryl alcohols to afford alkenes and alkynes in good to excellent yields. This protocol features excellent atom economy since alcohols and organotrifluoroborates react in a 1:1 ratio. Functional group tolerance superior to Lewis acid- and metal-catalyzed approaches was demonstrated. Furthermore, we were able to extend this method to 2-ethoxytetrahydrofuran which underwent direct substitution to afford functionalized furans in moderate to excellent yields. A variety of alkenyl- and alkynyltrifluoroborates readily participated in this transformation.","abstract_html":"Metal-free transformations of organotrifluoroborates are advantageous since they avoid using frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving organotrifluoroborates have emerged as an alternative to metal-catalyzed protocols. However, these methods rely on generating unstable boron dihalide species thereby resulting in low functional group tolerance. A Brønsted acid-catalyzed carbon-carbon bond forming methodology involving alkenyl- and alkynyltrifluoroborates and in situ generated carbocations has been developed. In the presence of HBF4, we have shown that organotrifluoroborates react with benzhydryl alcohols to afford alkenes and alkynes in good to excellent yields. This protocol features excellent atom economy since alcohols and organotrifluoroborates react in a 1:1 ratio. Functional group tolerance superior to Lewis acid- and metal-catalyzed approaches was demonstrated. Furthermore, we were able to extend this method to 2-ethoxytetrahydrofuran which underwent direct substitution to afford functionalized furans in moderate to excellent yields. A variety of alkenyl- and alkynyltrifluoroborates readily participated in this transformation.","abstract_has_math":false,"creators":["Fisher, Kayla M."],"institution":"University of Ontario Institute of Technology","degree_name":"Master of Science (MSc)","degree_level":null,"degree_discipline":"Applied Bioscience","degree_department":null,"school":null,"contributors":[],"advisors":["Bolshan, Yuri"],"committee_chairs":[],"committee_members":[],"year":2016,"date_issued":"2016-06-01","date_published":"2016-06-01","updated_at":"2026-07-24T05:35:41Z","subjects":["Brønsted acid","Organotrifluoroborates","Alkynylation","Alkenylation","Metal-free"],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10155/694","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Bolshan, Yuri"]},{"key":"dc:creator","label":"Author","values":["Fisher, Kayla M."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2016-12-15T14:50:38Z","2022-03-29T17:34:02Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2016-12-15T14:50:38Z","2022-03-29T17:34:02Z"]},{"key":"dc:date.issued","label":"Date","values":["2016-06-01"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Applied Bioscience"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MSc)"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Ontario Institute of Technology"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Brønsted acid","Organotrifluoroborates","Alkynylation","Alkenylation","Metal-free"]}]},{"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/10155/694"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Metal-free transformations of organotrifluoroborates are advantageous since they avoid using frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving organotrifluoroborates have emerged as an alternative to metal-catalyzed protocols. However, these methods rely on generating unstable boron dihalide species thereby resulting in low functional group tolerance. A Brønsted acid-catalyzed carbon-carbon bond forming methodology involving alkenyl- and alkynyltrifluoroborates and in situ generated carbocations has been developed. In the presence of HBF4, we have shown that organotrifluoroborates react with benzhydryl alcohols to afford alkenes and alkynes in good to excellent yields. This protocol features excellent atom economy since alcohols and organotrifluoroborates react in a 1:1 ratio. Functional group tolerance superior to Lewis acid- and metal-catalyzed approaches was demonstrated. Furthermore, we were able to extend this method to 2-ethoxytetrahydrofuran which underwent direct substitution to afford functionalized furans in moderate to excellent yields. A variety of alkenyl- and alkynyltrifluoroborates readily participated in this transformation."]},{"key":"dc:title","label":"Title","values":["Direct Brønsted acid-catalyzed functionalization of benzhydryl alcohols and 2-ethoxytetrahydrofuran using potassium trifluoroborate salts"]}]}],"canonical_facts":{"dc:contributor.advisor":["Bolshan, Yuri"],"dc:creator":["Fisher, Kayla M."],"dc:date.accessioned":["2016-12-15T14:50:38Z","2022-03-29T17:34:02Z"],"dc:date.available":["2016-12-15T14:50:38Z","2022-03-29T17:34:02Z"],"dc:date.issued":["2016-06-01"],"dc:description.abstract":["Metal-free transformations of organotrifluoroborates are advantageous since they avoid using frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving organotrifluoroborates have emerged as an alternative to metal-catalyzed protocols. However, these methods rely on generating unstable boron dihalide species thereby resulting in low functional group tolerance. A Brønsted acid-catalyzed carbon-carbon bond forming methodology involving alkenyl- and alkynyltrifluoroborates and in situ generated carbocations has been developed. In the presence of HBF4, we have shown that organotrifluoroborates react with benzhydryl alcohols to afford alkenes and alkynes in good to excellent yields. This protocol features excellent atom economy since alcohols and organotrifluoroborates react in a 1:1 ratio. Functional group tolerance superior to Lewis acid- and metal-catalyzed approaches was demonstrated. Furthermore, we were able to extend this method to 2-ethoxytetrahydrofuran which underwent direct substitution to afford functionalized furans in moderate to excellent yields. A variety of alkenyl- and alkynyltrifluoroborates readily participated in this transformation."],"dc:identifier.uri":["https://hdl.handle.net/10155/694"],"dc:language.iso":["en"],"dc:subject":["Brønsted acid","Organotrifluoroborates","Alkynylation","Alkenylation","Metal-free"],"dc:title":["Direct Brønsted acid-catalyzed functionalization of benzhydryl alcohols and 2-ethoxytetrahydrofuran using potassium trifluoroborate salts"],"dc:type":["Thesis"],"thesis:degree_discipline":["Applied Bioscience"],"thesis:degree_name":["Master of Science (MSc)"],"thesis:institution_name":["University of Ontario Institute of Technology"]},"updated_at":"2026-07-24T05:35:41Z"}