{"id":{"repo_id":"uoit","oai_identifier":"oai:ontariotechu.scholaris.ca:10155/2001"},"canonical_url":"https://search.dev.ndltd.org/etd/uoit/oai:ontariotechu.scholaris.ca:10155/2001","repository":{"repo_id":"uoit","name":"Ontario Institute of Technology","base_url":"https://ontariotechu.scholaris.ca/server/oai/request"},"display":{"title":"Brønsted acid-catalyzed alkylation of tetrazoles with alcohols","abstract":"Tetrazoles hold significant pharmaceutical importance, being a key component in various drugs with hypertensive, antimicrobial, antiviral, antiallergic, cytostatic and nootropic biological activities. Traditionally, tetrazoles have been alkylated using alkyl halides under basic conditions. However, alcohols are the most convenient alkylating reagents. While Lewis and Brønsted acid-catalyzed alkylations of tetrazoles using alcohols have been reported, their drawbacks include the necessity to use excess of strong Brønsted acid, narrow scope, long reaction time and poor functional group tolerance. Recently, we developed a methodology for the alkylation of 5-substituted tetrazoles with benzhydryl and benzylic alcohols in the presence of 5 mol% of a mild Brønsted acid catalyst HBF4 (aq). The developed protocol features low acid catalyst loading, short reaction times, generally high yields and high N2 selectivity. In addition, the developed methodology exhibits excellent functional group tolerance.","abstract_html":"Tetrazoles hold significant pharmaceutical importance, being a key component in various drugs with hypertensive, antimicrobial, antiviral, antiallergic, cytostatic and nootropic biological activities. Traditionally, tetrazoles have been alkylated using alkyl halides under basic conditions. However, alcohols are the most convenient alkylating reagents. While Lewis and Brønsted acid-catalyzed alkylations of tetrazoles using alcohols have been reported, their drawbacks include the necessity to use excess of strong Brønsted acid, narrow scope, long reaction time and poor functional group tolerance. Recently, we developed a methodology for the alkylation of 5-substituted tetrazoles with benzhydryl and benzylic alcohols in the presence of 5 mol% of a mild Brønsted acid catalyst HBF4 (aq). The developed protocol features low acid catalyst loading, short reaction times, generally high yields and high N2 selectivity. In addition, the developed methodology exhibits excellent functional group tolerance.","abstract_has_math":false,"creators":["Butt, Arsala"],"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":2025,"date_issued":"2025-08-01","date_published":"2025-08-01","updated_at":"2026-07-24T05:35:20Z","subjects":[],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10155/2001","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":["Butt, Arsala"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2025-09-19T15:32:29Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2025-09-19T15:32:29Z"]},{"key":"dc:date.issued","label":"Date","values":["2025-08-01"]},{"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":"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/10155/2001"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Tetrazoles hold significant pharmaceutical importance, being a key component in various drugs with hypertensive, antimicrobial, antiviral, antiallergic, cytostatic and nootropic biological activities. Traditionally, tetrazoles have been alkylated using alkyl halides under basic conditions. However, alcohols are the most convenient alkylating reagents. While Lewis and Brønsted acid-catalyzed alkylations of tetrazoles using alcohols have been reported, their drawbacks include the necessity to use excess of strong Brønsted acid, narrow scope, long reaction time and poor functional group tolerance. Recently, we developed a methodology for the alkylation of 5-substituted tetrazoles with benzhydryl and benzylic alcohols in the presence of 5 mol% of a mild Brønsted acid catalyst HBF4 (aq). The developed protocol features low acid catalyst loading, short reaction times, generally high yields and high N2 selectivity. In addition, the developed methodology exhibits excellent functional group tolerance."]},{"key":"dc:title","label":"Title","values":["Brønsted acid-catalyzed alkylation of tetrazoles with alcohols"]}]}],"canonical_facts":{"dc:contributor.advisor":["Bolshan, Yuri"],"dc:creator":["Butt, Arsala"],"dc:date.accessioned":["2025-09-19T15:32:29Z"],"dc:date.available":["2025-09-19T15:32:29Z"],"dc:date.issued":["2025-08-01"],"dc:description.abstract":["Tetrazoles hold significant pharmaceutical importance, being a key component in various drugs with hypertensive, antimicrobial, antiviral, antiallergic, cytostatic and nootropic biological activities. Traditionally, tetrazoles have been alkylated using alkyl halides under basic conditions. However, alcohols are the most convenient alkylating reagents. While Lewis and Brønsted acid-catalyzed alkylations of tetrazoles using alcohols have been reported, their drawbacks include the necessity to use excess of strong Brønsted acid, narrow scope, long reaction time and poor functional group tolerance. Recently, we developed a methodology for the alkylation of 5-substituted tetrazoles with benzhydryl and benzylic alcohols in the presence of 5 mol% of a mild Brønsted acid catalyst HBF4 (aq). The developed protocol features low acid catalyst loading, short reaction times, generally high yields and high N2 selectivity. In addition, the developed methodology exhibits excellent functional group tolerance."],"dc:identifier.uri":["https://hdl.handle.net/10155/2001"],"dc:language.iso":["en"],"dc:title":["Brønsted acid-catalyzed alkylation of tetrazoles with 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":"2026-07-24T05:35:20Z"}