Arenophile-mediated dearomative functionalization of unactivated arenes
Wertjes, William Charles
Loading…
Permalink
https://hdl.handle.net/2142/109489
Description
Title
Arenophile-mediated dearomative functionalization of unactivated arenes
Author(s)
Wertjes, William Charles
Issue Date
2020-11-24
Director of Research (if dissertation) or Advisor (if thesis)
Sarlah, David
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
M.S.
Degree Level
Thesis
Keyword(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.
Use this login method if you
don't
have an
@illinois.edu
email address.
(Oops, I do have one)
IDEALS migrated to a new platform on June 23, 2022. If you created
your account prior to this date, you will have to reset your password
using the forgot-password link below.
