Contact
Dr. Michael W. Justik
Deparment of Chemistry
School of Science
Penn State Erie
The Behrend College
4205 College Drive
Erie PA, 16563-0203
(814)-898-6412
My research is primarily in the area of organic compounds based on hypervalent iodine. This interesting group of molecules includes [hydroxy(tosyloxy)iodo]benzene (Koser's reagent, HTIB), iodobenzene diacetate, and the Dess-Martin periodane. These and many related compounds have achieved the status of "reagent" in contemporary synthetic methods. Due to the higher oxidation state of iodine, these compounds act as mild oxidants capable of an ever expanding scope of synthetic applications. With the recent interest in "green" methods of organic synthesis my focus is the development and study of a cyclic analog of HTIB, 1H-1-hydroxy-1,2,3-benziodoxathiole 3,3-dioxide or HMBI. When an oxidant such as HTIB is used, it becomes reduced, in this case to iodobenene and p-toluenesulfonic acid. In a synthetic procedure this requires an aqueous workup to remove the acid, and often column chromatography to remove the iodobenzene. Due to the high vapor pressure of iodobenzene it is partially lost in concentration under vacuum and is rarely collected and reused or even disposed of properly! HMBI Upon reduction only yields a iodinated toluenesulfonic acid, which can be recovered quantitatively and reused. In fact, the HMBI used for my current research is reoxidized and reutilized reagent from earlier projects!
This reagent is very applicable to the undergraduate reseach program here at Behrend. With the simplified work-up procedures this reagent offers, an undergraduate can spend more of their limited time doing research focused on reaction outcome and product separation and distribution rather than tedious and repetitive workup procedures for the reagent itself.
With the development of the recyclable reagent projects well underway, my research laboratory is now pursuing the preparation of novel iodinanes for analysis by X-ray crystallography. The structural features of hypervalent iodine compounds, such as the geometric distribution of ligands, bond lengths and bond angles, dictate their chemistry. Collobroation with Dr. John Protasiewicz at Case Western Reserve Univerisity and use of his X-ray facility has already been fruitful. Our preparation and sturctural characterization of 2-[(aryl)iodonio]benzenesulfonates has just been accepted for publication in Tetrahedron Letters. These compounds have great potential for being recycleable carriers for aryl groups in metal catalyzed Suzuki-Myamura and Sonogashira cross coupling reactions.
