Dr. DeBoef`s CV - URI Department of Chemistry

BIOGRAPHICAL SKETCH Provide the following information for the Senior/key personnel and other significant contributors in the order listed on Form Page 2. Follow this format for each person. DO NOT EXCEED FOUR PAGES.

Brenton DeBoef

Associate Professor

EDUCATION/TRAINING INSTITUTION AND LOCATION

Evangel University Washington University in St. Louis Washington University in St. Louis Columbia University

DEGREE (if applicable)

MM/YY

B.S. A.M. Ph.D. Postdoc

05/98 05/2001 05/2003 06/2005

FIELD OF STUDY

Chemistry, Mathematics Organic Chemistry Organic Chemistry Organometallic Chemistry

A. Personal Statement Research in the DeBoef group spans the fields of organic and organometallic chemistry and attempts to use these tools for solving medicinal and pharmaceutical problems. These efforts are divided into two separate research programs: 1) Development of New Reactions Using C-H Functionalization, and 2) Development of MRI Contrast Agents for Monitoring Biochemistry in Vivo. My research team and I are experts at synthesizing heterocyclic compounds like the majority of modern drugs. In the past five years, I have mentored 10 graduate and over 20 undergraduate students. The graduate students who have matriculated with M.S. (5) and Ph.D. (2) degrees are employed at pharmaceutical or biotech companies and the NIH. I have also developed and published new chemical education material in the Journal of Chemical Education. B. Positions and Honors Positions and Employment Summer 1996 Summer 1997 Summer 1998 1998-2000 2000-2003 2003-2005 2005-2011 2011-Present

NSF-REU Fellow, University of Arkansas, Fayetteville, Arkansas NSF-REU Fellow, Columbia University, New York, New York Undergraduate Research Assistant, P&G Pharmaceuticals, Mason, Ohio Teaching Assistant, Washington University, St. Louis, Missouri Research Assistant, Washington University, St. Louis, Missouri Postdoctoral Fellow, Columbia University, New York, New York Assistant Professor, University of Rhode Island, Kingston, Rhode Island Associate Professor, University of Rhode Island, Kingston, Rhode Island

Other Experience and Professional Memberships American Chemical Society (member) Sigma Xi (faculty sponsor)

Honors 1994-1998 1998 1998 1999 2005 2008 2009 2011 2011

Dean's List, Evangel College (every semester) Summa Cum Laude, Evangel College Outstanding Chemistry Graduate, Evangel College Departmental Award for Teaching Excellence, Washington University NRSA Postdoctoral Fellowship, NIGMS (declined, so I could accept the position at URI) Outstanding Young Alumnus, Evangel University NSF CAREER Award Thieme Chemistry Journal Awardee Pfizer Green Chemistry Award

Service on Governmental Review Panels 2011 2011

Reviewer, NSF Panel on Organic Synthesis Reviewer, NIH Synthetic and Biological Chemistry Study Section (SBCB)

C. Peer-reviewed Publications Highest Impact publications (Independent career) 1.

Timothy A. Dwight, Nicholas. R. Rue†, Dagmara Charyk†, Ryan Josselyn† and Brenton DeBoef*, “C-C Bond Formation via Double C-H Functionalization: Aerobic Oxidative Coupling as a Method for Synthesizing Heterocoupled Biaryls” Org. Lett., 2007, 9, 3137-31319.

2.

Shathaverdhan Potavathri, Timothy A. Dwight, Ashley Dumas, Gregory Naumiec, Jeffery Hammann†‡ and Brenton DeBoef*, "Oxidant Controlled Regioselectivity in the Oxidative Arylation of N-Acetylindoles," Tetrahedron Lett. 2008, 49, 4050-4053.

3.

Shathaverdhan Potavathri, Kyle C. Pereira, Serge I. Gorelsky, Andrew Pike, † Alexis P. LeBris, and Brenton DeBoef* “Regioselective Oxidative Arylation of Indoles Bearing N-Alkyl Protecting Groups: Dual C−H Functionalization via a Concerted Metalation−Deprotonation Mechanism,” J. Am. Chem. Soc. 2010, 132, 14676–14681.

4.

Shathaverdhan Potavathri, Abhishek Kantak and Brenton DeBoef* “Increasing synthetic efficiency via direct C-H functionalization: Formal synthesis of an inhibitor of botulinum neurotoxin,” Chem. Commun. 2011, 47, 4679-4681.

5.

Metal-Free Intermolecular Oxidative C-N Bond Formation via Tandem C-H / N-H Bond Activation. Abhishek A. Kantak, Shathaverdhan Potavathri, Rose A. Barham, Kaitlyn M. Romano and Brenton DeBoef, submitted to J. Am. Chem. Soc. 2011, 133,19960-19965. * corresponding author(s) † undergraduate author ‡ visiting international student All other co-authors are graduate students.

Additional recent publications of importance to the field (in chronological order) 1.

Scott R. Gilbertson* and Brenton DeBoef, “Rhodium Catalyzed [4+2+2] Cycloaddition and Alkyne Insertion: A Novel Route to Eight-Membered Rings,” J. Am. Chem. Soc., 2002, 124, 8784-8785.

2.

Brenton DeBoef, Stefan J. Pastine and Dalibor Sames*, “Cross-Coupling of sp3 C-H Bonds and Alkenes: Catalytic Cyclization of Alkene-Amide Substrates,” J. Am. Chem. Soc., 2004, 126, 6556-6557.

3.

Brenton DeBoef, W. Richard Counts and Scott R. Gilbertson*, “Rhodium Catalyzed Synthesis of EightMember Rings” J. Org. Chem., 2007, 72, 799-804.

4.

Hegner, Jessica,† Kyle C. Pereira, Brenton DeBoef* and Brett L. Lucht* "Conversion of Cellulose to Glucose and Levulinic Acid Via Solid-Supported Acid Catalysis," Tetrahedron Lett. 2010, 51, 2356-2358.

5.

Joshua Potvin, † Erin Sorlien, † Jessica Hegner, † Brenton DeBoef*, Brett L. Lucht*, “Effect of NaCl on the conversion of cellulose to glucose and levulinic acid via solid supported acid catalysis “ Tetrahedron Lett., 2011, 52, 5891-5893.

D. Research Support Ongoing Research Support Faculty Early Career Development (CAREER) 2/1/2009 – 1/31/2014 National Science Foundation CAREER: Oxidative Cross-Coupling--An Efficient and Green Method for Synthesizing Biaryls This proposal describes efforts to develop novel palladium catalyzed coupling reactions. Role: PI R15 AREA Award NIH (NIGMS) 12/1/2010 – 11/30/2013 New Methods for Synthesis via Oxidative Coupling This proposal describes the development of methods to create C-C and C-N bonds via oxidative C-H functionalization reactions. Specific aims 1 and 3 of the current R01 proposal overlap with specific aims 1 and 3 of this R15 award. If the current proposal were funded, URI would return the remainder of the R15 award in order to accept the R01 award with no conflicts of interest. Role: PI DoD (USAF) 8/17/2011 – 5/16/2012 Selective Oxidation of Heterocyclic Amines This proposal describes methods to selectively oxidize diamine substrates to mononitro, monoamines. The use of cyclic voltammetry to monitor this process is also described. Role: Subcontract. Primary STTR award to Nalas Enineering. Completed Research Support PRF-G 7/1/2007-6/30/2009 Petroleum Research Fund Synthesis of Bis-arenes via Oxidative Coupling This study investigated the mechanisms of palladium catalyzed oxidative coupling reactions. Role: PI Pilot/Feasibility Program 5/1/2008-4/30/2009 Rhode Island INBRE Program (Subsidiary of NIH EBSCOR Program) Synthesis of Next-Generation Inhibitors of Botulinum Neurotoxin This proposal described the synthesis of a series of arylated indoles and their evaluation as inhibitors of Botulinum neurotoxin using the oxidative coupling technology developed in the DeBoef laboratory. Role: PI Research Proposal Development 7/1/2008-12/31/2008 University of Rhode Island Development of an MRI Contrast Agent for Dopamine Transporter This proposal described the development of contrast agents for visualizing DAT using gadolinium complexes (not HP-Xe, as in this proposal). Role: PI