{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/109489"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/109489","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Arenophile-mediated dearomative functionalization of unactivated arenes","abstract":"Two photomediated dearomative methods are reported using an “arenophile” called MTAD. Arene-arenophile cycloadducts are formed by irradiation of mixtures of unactivated arenes and MTAD at cryogenic temperatures with visible light. These cycloadducts are subsequently used as substrates in metal-catalyzed transformations. In chapter one a palladium-catalyzed dearomative syn- 1,4-diamination of unactivated arenes is presented using simple amine nucleophiles. An enantioselective variant and a number of elaborations of the resulting products are exhibited. In chapter two a concise two-step procedure to access oxepines from simple arenes is disclosed, enabled by a manganese(II)-catalyzed epoxidation of the arene-arenophile cycloadducts. Studies toward utilizing this method in concise syntheses of natural products perilloxin and fortimicin A are also reported.","abstract_html":"Two photomediated dearomative methods are reported using an “arenophile” called MTAD. Arene-arenophile cycloadducts are formed by irradiation of mixtures of unactivated arenes and MTAD at cryogenic temperatures with visible light. These cycloadducts are subsequently used as substrates in metal-catalyzed transformations. In chapter one a palladium-catalyzed dearomative syn- 1,4-diamination of unactivated arenes is presented using simple amine nucleophiles. An enantioselective variant and a number of elaborations of the resulting products are exhibited. In chapter two a concise two-step procedure to access oxepines from simple arenes is disclosed, enabled by a manganese(II)-catalyzed epoxidation of the arene-arenophile cycloadducts. Studies toward utilizing this method in concise syntheses of natural products perilloxin and fortimicin A are also reported.","abstract_has_math":false,"creators":["Wertjes, William Charles"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"M.S.","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Sarlah, David"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2021,"date_issued":"2021-03-05T21:40:42Z","date_published":"2021-03-05T21:40:42Z","updated_at":"2026-07-22T22:24:50Z","subjects":["dearomatization","arenophile","arene","aromatic"],"languages":["en"],"rights":["Copyright 2020 William Wertjes"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/2142/109489","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Sarlah, David"]},{"key":"dc:creator","label":"Author","values":["Wertjes, William Charles"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2021-03-05T21:40:42Z","2023-03-05T21:43:00Z","2020-11-24","2020-12"]},{"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":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M.S."]},{"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":["dearomatization","arenophile","arene","aromatic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 2020 William Wertjes"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/109489"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Two photomediated dearomative methods are reported using an “arenophile” called MTAD. Arene-arenophile cycloadducts are formed by irradiation of mixtures of unactivated arenes and MTAD at cryogenic temperatures with visible light. These cycloadducts are subsequently used as substrates in metal-catalyzed transformations. In chapter one a palladium-catalyzed dearomative syn- 1,4-diamination of unactivated arenes is presented using simple amine nucleophiles. An enantioselective variant and a number of elaborations of the resulting products are exhibited. In chapter two a concise two-step procedure to access oxepines from simple arenes is disclosed, enabled by a manganese(II)-catalyzed epoxidation of the arene-arenophile cycloadducts. Studies toward utilizing this method in concise syntheses of natural products perilloxin and fortimicin A are also reported.","Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2022-12-01","The student, William Wertjes, accepted the attached license on 2020-11-11 at 23:25.","The student, William Wertjes, submitted this Thesis for approval on 2020-11-11 at 23:42.","This Thesis was approved for publication on 2020-11-24 at 09:03.","DSpace SAF Submission Ingestion Package generated from Vireo submission #15876 on 2021-03-04 at 16:19:28","Made available in DSpace on 2021-03-05T21:40:42Z (GMT). No. of bitstreams: 2 WERTJES-THESIS-2020.pdf: 30917180 bytes, checksum: e99e05912854366786242b74a7eaed9c (MD5) LICENSE.txt: 4212 bytes, checksum: 4547de2ef8084a3337f904124c99c2a9 (MD5) Previous issue date: 2020-11-24","Embargo set by: Seth Robbins for item 117193 Lift date: 2023-03-05T21:40:52Z Reason: Author requested U of Illinois access only (OA after 2yrs) in Vireo ETD system","Embargo set by: Seth Robbins for item 117193 Lift date: 2023-03-05T21:43:00Z Reason: Author requested U of Illinois access only (OA after 2yrs) in Vireo ETD system","Author requested U of Illinois access only (OA after 2yrs) in Vireo ETD system","U of I Only"]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Arenophile-mediated dearomative functionalization of unactivated arenes"]}]}],"canonical_facts":{"dc:contributor":["Sarlah, David"],"dc:creator":["Wertjes, William Charles"],"dc:date":["2021-03-05T21:40:42Z","2023-03-05T21:43:00Z","2020-11-24","2020-12"],"dc:description":["Two photomediated dearomative methods are reported using an “arenophile” called MTAD. Arene-arenophile cycloadducts are formed by irradiation of mixtures of unactivated arenes and MTAD at cryogenic temperatures with visible light. These cycloadducts are subsequently used as substrates in metal-catalyzed transformations. In chapter one a palladium-catalyzed dearomative syn- 1,4-diamination of unactivated arenes is presented using simple amine nucleophiles. An enantioselective variant and a number of elaborations of the resulting products are exhibited. In chapter two a concise two-step procedure to access oxepines from simple arenes is disclosed, enabled by a manganese(II)-catalyzed epoxidation of the arene-arenophile cycloadducts. Studies toward utilizing this method in concise syntheses of natural products perilloxin and fortimicin A are also reported.","Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2022-12-01","The student, William Wertjes, accepted the attached license on 2020-11-11 at 23:25.","The student, William Wertjes, submitted this Thesis for approval on 2020-11-11 at 23:42.","This Thesis was approved for publication on 2020-11-24 at 09:03.","DSpace SAF Submission Ingestion Package generated from Vireo submission #15876 on 2021-03-04 at 16:19:28","Made available in DSpace on 2021-03-05T21:40:42Z (GMT). No. of bitstreams: 2 WERTJES-THESIS-2020.pdf: 30917180 bytes, checksum: e99e05912854366786242b74a7eaed9c (MD5) LICENSE.txt: 4212 bytes, checksum: 4547de2ef8084a3337f904124c99c2a9 (MD5) Previous issue date: 2020-11-24","Embargo set by: Seth Robbins for item 117193 Lift date: 2023-03-05T21:40:52Z Reason: Author requested U of Illinois access only (OA after 2yrs) in Vireo ETD system","Embargo set by: Seth Robbins for item 117193 Lift date: 2023-03-05T21:43:00Z Reason: Author requested U of Illinois access only (OA after 2yrs) in Vireo ETD system","Author requested U of Illinois access only (OA after 2yrs) in Vireo ETD system","U of I Only"],"dc:format":["application/pdf"],"dc:identifier":["http://hdl.handle.net/2142/109489"],"dc:language":["en"],"dc:rights":["Copyright 2020 William Wertjes"],"dc:subject":["dearomatization","arenophile","arene","aromatic"],"dc:title":["Arenophile-mediated dearomative functionalization of unactivated arenes"],"dc:type":["text","Thesis"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["M.S."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:24:50Z"}