Timothy Funk

Research Interests:

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 discoverd 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)

  1. *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.
  2. *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.
  3. *Moyer, S. A.; Funk, T. W. "Air-Stable Iron Catalyst for the Oppenauer-Type Oxidation of Alcohols." Tetrahedron Letters 2010, 51, 5430-5433.
  4. 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.

 

Timothy Funk

Timothy Funk
Associate Professor, Chemistry

Email: tfunk@gettysburg.edu
Phone: (717) 337 - 6348

Box: Campus Box 0393

Address: Science Center
Room 243
300 North Washington St.
Gettysburg, PA 17325-1400

Education:
PhD California Institute of Technology, 2006
BS Gettysburg College, 2000

Academic Focus:
organic chemistry, organometallic catalysis