Research - Dr. Justik’s Group

1. Research - Dr. Justik’s Group Synthesis and Structure of Hypervalent Iodine Compounds

2. Hypervalent Iodine Compounds • The concept “hypervalent iodine” refers to the unique bonding interaction in iodine(III) and (V) compounds:

3. Hypervalent Iodine Compounds • Hypervalent iodine oxidants were the original “green” reagents replacing many toxic metals (lead and thallium) in important synthetic transformations:

4. Resaerch Interests Synthesis and Reactivity Structure In collaboration with Dr. John Protasiewicz at Case Western Reserve University explore new iodinanes using X-ray crystallography Characterize novel iodinanes of interest from an intellectual curiosity or synthetic challenge aspect • Improvement of “green” synthetic methodology using hypervalent iodine • Exploration of hetereocyclic syntheses • Preparation of novel iodinanes of interest from an intellectual curiosity or synthetic challenge aspect

5. Synthesis with Hypervalent Iodine 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-Dioxide HMBI A compact heterocyclic equivalent of HTIB MW 314.10 g/mol Hydroxy(tosyloxy)iodobenzene“Koser’s Reagent” HTIB A mild and useful oxidant that mimics elemental bromine MW 392.22 g/mol

6. Synthesis with Hypervalent Iodine Improving “green” methods with HMBI - MWJ

7. Synthesis with Hypervalent Iodine

8. Synthesis with Hypervalent Iodine • Heterocyclic Synthesis

9. Synthesis with Hypervalent Iodine • Heterocyclic Synthesis (Melanie Knowlton ’10, Rachael Carmichael ‘12)

10. Synthesis with Hypervalent Iodine • Attempted Heterocyclic Synthesis – (Heather Sopher ‘09, Samantha Kristufek ’11?)

11. Synthesis with Hypervalent Iodine • Attempted Heterocyclic Synthesis – (Heather Sopher ‘09, Samantha Kristufek ’11)

12. Synthesis with Hypervalent Iodine • Heterocyclic Synthesis

13. Synthesis with Hypervalent Iodine • Synthesis of a Novel Phenyliodonium Betaine - MWJ

14. Synthesis with Hypervalent Iodine • Synthesis of a Novel Phenyliodonium Betaine - MWJ Brianne Sawders (‘12) is currently exploring the limits of the Suzuki reaction with this betaine

15. Synthesis with Hypervalent Iodine • Other long-term targets of interest

16. Structural Studies • Structural Confirmation of an alkenyliodonium salt with a pyridine N-oxide moiety

17. Structural Studies • Synthesis of a novel phenyliodinium betaine

18. Structural Studies • First example of a protonated iodosobenzene derivative

19. Acknowledgements • My Students: • Michelle Borkovec‘06 • Alyssa Zimmerman ‘08. • Heather Sopher’09 • Michael Hughes ’09 • Amanda Dechant’09 • Alex Ekstrom(biology) ’08 • Melanie Knowlton ’09 • Rocky Viggiano‘09 • Samantha Kristufek’11 • Danielle Bittner ’11 • Rachael Carmichael ’12 • Brianne Sawders’12 • Brandon Blanchard ‘12 • Kathryn Sauka ‘14 • Alexis Rowley‘15 • Nick Burton‘15 • Anita Brkic’15 • Johnny Lorigan’15 • Zak Ekstrom’15