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Development of New Methods for Visible Light-Induced Activation of C-I, C-O, and S-O Bonds

thesis
posted on 01.08.2019 by Maxim Ratushnyy
This thesis consists of three parts. The first part describes the development of the mild, visible light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade reaction of vinyl iodides. The method features a formation of previously unknown vinyl hybrid palladium-radical intermediates, capable of a 1,5-HAT process. Overall, the transformation leads to the formation of iodomethyl carbo- and heterocyclic products. The second part of this thesis communicates the development of visible light-induced sulfonylation reaction of vinylarenes with arylsulfonate phenol esters. This protocol operates via new mode of the S−O bond activation, thus constituting a novel reactivity of readily available arylsulfonate esters. The transformation leads to a variety aromatic vinyl sulfones in efficient manner. The third part describes the development of visible light-induced palladium-catalyzed intramolecular C(sp2)−X/C(sp3)−H coupling reaction of aryl triflates leading to a variety of 3,3-di- and 3-monosubstituted oxindole motifs. This method illustrates the first example of the visible light-induced palladium-catalyzed activation of C−O bond leading to the aryl hybrid palladium-radical intermediates. This transformation substantially expands the inventory of organic electrophilic partners for the visible light palladium catalysis.

History

Advisor

Gevorgyan, Vladimir

Chair

Gevorgyan, Vladimir

Department

Chemistry

Degree Grantor

University of Illinois at Chicago

Degree Level

Doctoral

Degree name

PhD, Doctor of Philosophy

Committee Member

Lee, Daesung Mohr, Justin T Mankad, Neal P Cho, Hee Yeon

Submitted date

August 2019

Thesis type

application/pdf

Language

en

Issue date

29/05/2019

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