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Title:Arenophile-mediated dearomative functionalization of unactivated arenes
Author(s):Wertjes, William Charles
Advisor(s):Sarlah, David
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:M.S.
Genre:Thesis
Subject(s):dearomatization
arenophile
arene
aromatic
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.
Issue Date:2020-11-24
Type:Thesis
URI:http://hdl.handle.net/2142/109489
Rights Information:Copyright 2020 William Wertjes
Date Available in IDEALS:2021-03-05
Date Deposited:2020-12


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