Dr. Scott Handy

CONTACT INFO:

E-mail: Scott.Handy@mtsu.edu
Phone: (615) 904-8114
Office: Davis Science Bldg. 228C
P.O. Box : 68

EDUCATION:

BS University of Iowa (1991)
PhD Indiana University, Paul Grieco, advisor (1996)
NIH Postdoctoral Fellow, Stanford University, Paul Wender, advisor (1996-1999)
Assistant Professor, Binghamton University (1999-2005)

RESEARCH INTEREST:

My basic area of research interest is Organic Synthesis. Within this broad area, I have two areas current focus: Room temperature ionic liquids (RTILs) and regioselective polycoupling reactions on heteroaromatics.

For the RTIL project, work to date has focused on using these materials as replacements for either volatile, toxic organic solvents or for petroleum-based support materials. While there is still work to do in these areas, the future thrust of this research will be more focused on combining green (aka environmentally compatible) RTILs with another green synthetic method - electrosynthesis. This combination will serve to eliminate solvent and electrolyte waste by having a recyclable solvent/electrolyte (the RTIL) and reagent waste by using electricity as the reagent (the electrosynthesis part). What is required is the development of less viscous RTILs, to avoid the necessity of including volatile organic co-solvents in the reaction. Further, preliminary results have shown that there appears to be a clear viscosity level below which the RTIL can be recycled and above which it is partially decomposed. Efforts to determine the generality of this value will have a major impact on the application of RTILs and other alternative solvents in electrosynthesis.

For the regioselective polycoupling project, work to date has focused on discovering conditions that can be used to regioselectively couple one bromide in a di- or tri-bromoheteroaromatic. From these efforts, and the few other similar cases reported in the literature, a general predictive rule for the order of coupling has been developed. This rule uses the 1H NMR chemical shifts of the parent non-halogenated heteroaromatic compound as the predictive rule, with the more electron deficient (more deshielded) sites coupling first. Amazingly, this simple rule correctly predicts all known examples of such couplings. The next stage in this research is to develop conditions that enable one-pot regioselective couplings of both bromides. Already, two versions have been developed, one that uses a ligand-free palladium system, which can be activated for the second coupling by the addition of a ligand, and the other one that uses a change in solvent mixture to catalyze the second coupling. Detailed understanding of the mechanistic implications of these changes and the application to other heteroaromatics and other types of cross-coupling reactions are an obvious next step for these studies. As systems are developed, their application to biologically interesting compounds, such as the lamellarins, Vioxx, Lipitor, and some combretastatin analogs, will be undertaken.

TEACHING:

CHEM 3010 Organic Chemistry I, CHEM 3020 Organic Chemistry II.

SELECTED PUBLICATIONS (last 2 years):

1. Handy, S.T.; Zhang, Y. "A Simple Guide for Predicting Regioselectivity in the Coupling of Polyhaloheteroaromatics." Chem. Commun. 2005, submitted.
2. Handy, S.T.; Zhang, Y. "The Lamellarins: Synthesis and Biological Activities."; Pure & Appl. Chem. 2005, in press.
3. Handy, S.T. "Room Temperature Ionic Liquids: Classes and Physical Properties." Curr. Org. Chem. 2005, 959-988. (Invited review based upon my research in the area of RTILs. Invitation by Atta-ur-Rahman, editor-in-chief.)
4. Handy, S.T. "A Simple Guide for Predicting Regioselectivity in the Coupling of Polyhaloheteroaromatics." Chem. Commun. 2005, submitted.
5. Handy, S.T.; Okello, M.; Bwambok, D. "Imidazolium Ionic Liquids: 2-Substitution and Acidity." In Sixteenth International Symposium on Molten Salts, Trulove, O.; DeLong, T.S.H., Eds. Electrochemical Society, 2005, In press.
6. Handy, S.T.; Omune, D. "A Chelation Effect on the Pathway between Intramoleculer Hydrodimerization and Pinacol Coupling." Org. Lett. 2005, 7, 1553-1555.
7. Handy, S.T.; Okello, M. "Homogeneous Supported Synthesis Using Ionic Liquid Supports: Tunable Separation Properties." J. Org. Chem. 2005, 70, 2874-2877.
8. Handy, S.T.; Okello, M. "The 2 Position of Imidazolium Ionic Liquids: Substitution and Exchange." J. Org. Chem. 2005, 70, 1915-1918.
9. Handy, S.T.; Sabatini, J.J.; Zhang, Y.; Vulfova, I. "Protection of poorly nucleophilic pyrroles." Tetrahedron Lett. 2004, 45, 5057-5060.
10. Handy, S.T.; Zhang, Y.; Bregman, H. "A modular synthesis of the lamellarins: Total synthesis of lamellarin G trimethyl ether." J. Org. Chem. 2004, 69, 2362-2366.

SELECTED PRESENTATIONS (last 2 years, national meetings only):

1. "Functionalized Ionic Liquids: Synthesis and Applications." 32nd Northeast Regional Meeting of the American Chemical Society, Rochester, NY, October 31-November 3, 2004.
2. "2-Substituted Imidazolium RTILs: Synthesis and Exchange." 32nd Northeast Regional Meeting of the American Chemical Society, Rochester, NY, October 31-November 3, 2004.
3. "Regioselective Couplings of Polyhaloheteroaromatics." 32nd Northeast Regional Meeting of the American Chemical Society, Rochester, NY, October 31-November 3, 2004.
4. "Intramolecular Hydrodimerization Reaction: Variations and Mechanistic Studies." 2004 Joint International Meeting (206th Meeting of the Electrochemical Society), Honolulu, Hawaii, October 3-8, 2004.
5. "Imidazolium Ionic Liquids: C2-Substitution and Acidity." 2004 Joint International Meeting (206th Meeting of the Electrochemical Society), Honolulu, Hawaii, October 3-8, 2004.
6. "Ionic Liquids as Supports." Special Symposium on Room Temperature Ionic Liquids, invitation by Professor Sanjay V. Malhotra, 228th National Meeting of the American Chemical Society, Philadelphia, August, 2004.
7. "The Intramolecular Hydrodimerization of Cyclic Enones." 6th Annual Baiser Symposium at the Electrochemical Society Meeting, San Antonio, Texas, May 2004.
8. "Synthesis of Differentially Substituted Pyrroles via Regioselective Couplings of Polyhalopyrroles."; Heterocyclic Compounds Gordon Research Conference, Salve Regina University, Newport, RI, July 4-9, 2004, Handy, S.T.

GRANTS AND AWARDS:

1. "Regioselective Polycoupling of Polyhaloheteroaromatics."; NIH AREA. Amount: $150,000. Duration: 12/01/05-11/30/08.
2. "Stegane: A Scaffold for New Anti-Cancer Agents." Leukemia Research Foundation, Amount: $64,171, Duration: July 1, 2002 - August 31, 2003.
3. "Novel Room-Temperature Ionic Liquids based on Biorenewable Resources", New York State Environmental Resources Development Agency (NYSERDA), Amount: $54,878, Duration: 09/01/01-08/31/02.