Chemistry, Department of
Department of Chemistry: Dissertations, Theses, and Student Research
First Advisor
Stephen G. DiMagno
Date of this Version
11-2015
Document Type
Thesis
Citation
A thesis presented to the faculty of the Graduate College at the University of Nebraska in partial fulfillment of requirements for the degree of Master of Science
Major: Chemistry
Under the supervision of Professor Stephen G. DiMagno
Lincoln, Nebraska, December 2015
Abstract
Aryl iodides have become widely recognized as versatile synthetic intermediates, owing to aromatic iodine’s excellent ability to participate in oxidative addition reactions. Iodoarenes readily undergo a variety of synthetic transformations including metal catalyzed cross-coupling reactions, diaryliodonium chemistry, formation of organometallics through reduction or metal-halogen exchange, as well as classical SN2 type chemistry. Because a wide array of transformations are available for aryl iodides, organic molecules containing this moiety often serve as vital precursors to highly desirable pharmaceuticals.
This thesis describes a simple and selective two-step approach to the formation of aryl iodides. This method proceeds through an easily purified diaryliodonium salt intermediate, which is subsequently converted to the corresponding aryl iodide. This method is an effective and general process for the selective synthesis of a large variety of monoiodinated arenes that are difficult to access by other approaches.
Advisor: Stephen G. DiMagno
Comments
Copyright © 2015, William H. Miller. Used by permission