My students and I are interested in the broad field of synthetic organic chemistry. Our three main areas of research include: 1) the synthesis of complex structures inspired by nature; 2) the application of transition metal catalysts to organic chemistry; and 3) the synthesis of organic polymers with photocleavable crosslinks.
Currently students are focused on developing air-stable (cyclopentadienone)iron di- and tricarbonyl compounds for use as reduction and oxidation catalysts. We have discovered that these compounds catalyze a variety of oxidative and reductive transformations including alcohol oxidations, ketone and aldehyde reductions, oxidative cyclizations of diols, and selective epoxide ring-openings. Catalyst design is at the heart of our work, and we are constantly thriving to develop more active, air-stable iron catalysts. Additionally, we are interested in understanding the mechanism of these iron-catalyzed reactions to aid in further catalyst development. We have also recently been spending time developing catalysts for selective cyclopropanol ring-opening reactions, synthesizing polymers with photocleavable crosslinks, and creating cleavable linkers for resin-bound, strained alkynes to aid in determining post-translational modification sites on proteins.
Recent Publications: (* denotes Gettysburg College undergraduate student)
- Funk, T. W.; *Mahoney, A. R.; *Sponenburg, R. A.; *Zimmerman, K. P.; *Kim, D. K.; *Harrison, E. E. Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations. Organometallics 2018, 37, 1133–1140.
- *Plank, T. N.; *Drake, J. L.; *Kim, D. K.; Funk, T. W. Air-Stable, Nitrile-Ligated (Cyclopentadienone)iron Dicarbonyl Compounds as Transfer Reduction and Oxidation Catalysts. Advanced Synthesis & Catalysis 2012, 354, 597-601.
- *Ziegler, D. T.; *Steffens, A. M.; Funk, T. W. Synthesis of alpha-Methyl Ketones by a Selective, Iridium-Catalyzed Cyclopropanol Ring-Opening Reaction. Tetrahedron Letters 2010, 51, 6726-6729.
- *Moyer, S. A.; Funk, T. W. Air-Stable Iron Catalyst for the Oppenauer-Type Oxidation of Alcohols. Tetrahedron Letters 2010, 51, 5430-5433.
- Funk, T. W. Enantioselective Synthesis of 5-epi-Citreoviral Using Ruthenium-Catalyzed Asymmetric Ring-Closing Metathesis. Organic Letters 2009, 11, 4998-5001.
Awarded External Grants
- American Chemical Society Petroleum Research Fund, “Development and Application of Air-Stable, Shvo-Type Iron Catalysts,” 9/1/2012–8/31/2015.
- Research Corporation for Science Advancement Single Investigator Cottrell College Science Award, “Transition Metal-Catalyzed Oxidations of Organic Molecules with Traditional Oxidants,” 7/2010–6/2012.
Chairperson/Associate Professor, Chemistry
Phone: (717) 337 - 6348
Box: Campus Box 0393
300 North Washington St.
Gettysburg, PA 17325-1400
PhD California Institute of Technology, 2006
BS Gettysburg College, 2000
organic chemistry, organometallic catalysis
Funk Group's Webpage