Chemistry, Department of


Date of this Version

Summer 8-1-2016


William Miller. Selective Iodination Using Diaryliodonium Salts. MS. Thesis, University of Nebraska-Lincoln, Lincoln, NE, 2016.


A THESIS Presented to the Faculty of The Graduate College at the University of Nebraska In partial Fulfillment of the Requirements For the Degree of Master of Science, Major: Chemistry, Under the Supervision of Professor Stephen G. DiMagno. Lincoln, Nebraska: August, 2016

Copyright (c) 2016 William H. Miller IV


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