Shaughnessy Group Research

The Shaughnessy group's interests are in the areas of organic and organometallic chemistry. We are interested in the mechanisms of organometallic reactions that are key steps in catalytic cycles. By understanding these fundamental reaction steps, we attempt to develop new or improved synthetic methods relying on organometallic catalysts. Areas of current interest include: environmentally benign catalytic systems, asymmetric metal-catalyzed reactions, cross-coupling reactions, novel bond forming reactions, biomolecle modification with metal catalysts. More specific descriptions of some current projects are listed below.

Novel ligands and solvent phases for aqueous-phase catalytic reactions.

We are interested in efforts to use "environmentally benign" solvents in metal-catalyzed reactions both to lessen the amount of waste produced and to allow recovery and recycling of the homogenous metal catalyst. The use of alternative solvents, such as water, ionic liquids, and fluorous solvents, have been explored with some success, although challenges remain. Our interests in this area are:

  • Design of water-soluble ligands with varied steric and electronic properties
  • Understanding the properties and coordination chemistry of these ligands
  • Applying these ligands in metal-catalyzed cross-coupling reactions
  • Using water-soluble catalysts in the modification of hydrophilic biomolecules, such as nucleosides.

Ionic liquid solvent effects on organometallic reactions

Ionic liquids (ILs) have attracted significant attention as potential alternative solvents. ILs offer some unique properties, such as a combination of potentially high polarity and low coordinating ability. We have been interested in studying fundamental organometallic reactions, such as oxidative addition, ligand substitution, and migratory insertion, IL solvents.

Mechanistic studies of organometallic reactions

We are always interested in understanding how organometallic reactions occur, so that we can design new or improved types of reactivity. Current targets for our studies include Rh-catalyzed coupling reactions and new classes of bond-forming reactions.

Applied Techniques

Students working in my group will learn a variety of skills that will prepare them for lives as independent sciencists. All students in my lab will become proficient in the following laboratory techniques:

  • Schlenk and Glovebox techniques. Methods for the handling and isolation of air-sensitive materials using both schlenk line and glovebox techniques.
  • Multi-step organic synthesis. Planning and carrying out multi-step syntheses of new organic ligands and substrates.
  • Inorganic and organometallic synthesis. Synthesis of known and new inorganic and organometallic compounds.
  • Techniques for compound characterization. The use of modern spectroscopic techniques for compound characterization, including GC, HPLC, multinuclear NMR, EPR, IR, UV-Vis, Mass Spectrometry, X-ray crystallography, and elemental analysis.

In addition, depending on student interests and the specific needs of the project, students will be exposed to:

  • Measurement of reaction kinetics. Techiques such as NMR, EPR, UV-Vis spectroscopy, GC, and HPLC will be used to determine concentrations of reaction species. These data will be used to determine reaction kinetics.
  • Parallel combinatorial synthesis. Use of combinatorial and/or parallel techniques to synthesis libraries of compounds. Characterization and screening of these compounds will also be carried out.
  • Electrochemistry. Use of electrochemical techniques to characterize and study redox active organometallic and organic compounds. Study of reaction kinetics by electrochemistry.

Outside the lab students in my group will be encouraged to become creative thinkers who can clearly communicate their ideas to both scientists and non-scientists. To facilitate this students will have regular opportunities to discuss both their own research as well as the literature in both formal and informal settings. Regular group meetings will allow students to discuss their research and the literature in a small informal setting. In addition to our department seminar series, students will be encouraged to give talks or posters at regional and national meetings.

Last updated on February 9, 2007

 
Page prepared by Dr. Kevin Shaughnessy
Associate Professor
The University of Alabama
 

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