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oai:www.ideals.illinois.edu:2142/109489 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Sarlah, David Wertjes, William Charles 2021-03-05T21:40:42Z 2021-03-05T21:40:42Z 2023-03-05T21:43:00Z 2020-11-24 2020-12 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 application/pdf http://hdl.handle.net/2142/109489 en Copyright 2020 William Wertjes dearomatization arenophile arene aromatic Arenophile-mediated dearomative functionalization of unactivated arenes text Thesis Chemistry Chemistry University of Illinois at Urbana-Champaign Thesis M.S.