{"id":{"repo_id":"uoit","oai_identifier":"oai:ontariotechu.scholaris.ca:10155/1160"},"canonical_url":"https://search.dev.ndltd.org/etd/uoit/oai:ontariotechu.scholaris.ca:10155/1160","repository":{"repo_id":"uoit","name":"Ontario Institute of Technology","base_url":"https://ontariotechu.scholaris.ca/server/oai/request"},"display":{"title":"Brønsted Acid-Catalyzed Reactions of Vinylboronic Acids and Benzhydryl Alcohols","abstract":"The functionalization of benzhydryl alcohols is an approach to form important building blocks in organic synthesis. More specifically, the derivatization of benzhydryl alcohols to afford an alkene is a desired approach due to the wide variety of derivatizations applicable to 1,3,3-triphenylpropene derivatives. However, many approaches towards functionalization rely on harsh reaction conditions or the use of Lewis acid catalysts, which leads to low functional group tolerance. Herein, a methodology for the formation of 1,3,3-triphenylpropene derivatives through a Brønsted acid-catalyzed reaction of styrylboronic acids and benzhydryl alcohols is reported. The use of tetrafluoroboric acid diethyl ether complex (HBF4·OEt2) in substoichiometric amounts is desirable as it allows for the introduction of the desired alkene structural motif under less harsh conditions than the previously reported methodologies. Using milder reaction conditions results in a broader scope of benzhydryl alcohols and styrylboronic acids as starting materials.","abstract_html":"The functionalization of benzhydryl alcohols is an approach to form important building blocks in organic synthesis. More specifically, the derivatization of benzhydryl alcohols to afford an alkene is a desired approach due to the wide variety of derivatizations applicable to 1,3,3-triphenylpropene derivatives. However, many approaches towards functionalization rely on harsh reaction conditions or the use of Lewis acid catalysts, which leads to low functional group tolerance. Herein, a methodology for the formation of 1,3,3-triphenylpropene derivatives through a Brønsted acid-catalyzed reaction of styrylboronic acids and benzhydryl alcohols is reported. The use of tetrafluoroboric acid diethyl ether complex (HBF4·OEt2) in substoichiometric amounts is desirable as it allows for the introduction of the desired alkene structural motif under less harsh conditions than the previously reported methodologies. Using milder reaction conditions results in a broader scope of benzhydryl alcohols and styrylboronic acids as starting materials.","abstract_has_math":false,"creators":["Barichello, Renata Olivia"],"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":2020,"date_issued":"2020-04-01","date_published":"2020-04-01","updated_at":"2026-07-24T05:35:24Z","subjects":["Styrylboronic Acid","Benzhydryl Alcohol","Brønsted Acid","Catalysis","Alkenylation"],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10155/1160","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":["Barichello, Renata Olivia"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2020-08-13T19:39:52Z","2022-03-29T17:25:59Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2020-08-13T19:39:52Z","2022-03-29T17:25:59Z"]},{"key":"dc:date.issued","label":"Date","values":["2020-04-01"]},{"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":["Styrylboronic Acid","Benzhydryl Alcohol","Brønsted Acid","Catalysis","Alkenylation"]}]},{"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/10155/1160"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The functionalization of benzhydryl alcohols is an approach to form important building blocks in organic synthesis. More specifically, the derivatization of benzhydryl alcohols to afford an alkene is a desired approach due to the wide variety of derivatizations applicable to 1,3,3-triphenylpropene derivatives. However, many approaches towards functionalization rely on harsh reaction conditions or the use of Lewis acid catalysts, which leads to low functional group tolerance. Herein, a methodology for the formation of 1,3,3-triphenylpropene derivatives through a Brønsted acid-catalyzed reaction of styrylboronic acids and benzhydryl alcohols is reported. The use of tetrafluoroboric acid diethyl ether complex (HBF4·OEt2) in substoichiometric amounts is desirable as it allows for the introduction of the desired alkene structural motif under less harsh conditions than the previously reported methodologies. Using milder reaction conditions results in a broader scope of benzhydryl alcohols and styrylboronic acids as starting materials."]},{"key":"dc:title","label":"Title","values":["Brønsted Acid-Catalyzed Reactions of Vinylboronic Acids and Benzhydryl Alcohols"]}]}],"canonical_facts":{"dc:contributor.advisor":["Bolshan, Yuri"],"dc:creator":["Barichello, Renata Olivia"],"dc:date.accessioned":["2020-08-13T19:39:52Z","2022-03-29T17:25:59Z"],"dc:date.available":["2020-08-13T19:39:52Z","2022-03-29T17:25:59Z"],"dc:date.issued":["2020-04-01"],"dc:description.abstract":["The functionalization of benzhydryl alcohols is an approach to form important building blocks in organic synthesis. More specifically, the derivatization of benzhydryl alcohols to afford an alkene is a desired approach due to the wide variety of derivatizations applicable to 1,3,3-triphenylpropene derivatives. However, many approaches towards functionalization rely on harsh reaction conditions or the use of Lewis acid catalysts, which leads to low functional group tolerance. Herein, a methodology for the formation of 1,3,3-triphenylpropene derivatives through a Brønsted acid-catalyzed reaction of styrylboronic acids and benzhydryl alcohols is reported. The use of tetrafluoroboric acid diethyl ether complex (HBF4·OEt2) in substoichiometric amounts is desirable as it allows for the introduction of the desired alkene structural motif under less harsh conditions than the previously reported methodologies. Using milder reaction conditions results in a broader scope of benzhydryl alcohols and styrylboronic acids as starting materials."],"dc:identifier.uri":["https://hdl.handle.net/10155/1160"],"dc:language.iso":["en"],"dc:subject":["Styrylboronic Acid","Benzhydryl Alcohol","Brønsted Acid","Catalysis","Alkenylation"],"dc:title":["Brønsted Acid-Catalyzed Reactions of Vinylboronic Acids and Benzhydryl Alcohols"],"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":"2026-07-24T05:35:24Z"}