Dr. Kevin Shaughnessy
  • 2072 Shelby Hall
  • (205) 348-4435
  • (205) 348-9104
Kevin Shaughnessy
Associate Professor / Department Chair
Education: Undergraduate Degree

BS, 1992, University of Nebraska

Education: Doctoral Degree

Ph.D., 1998, Stanford University

Education: Other

Postdoctoral Associate, 1997-1999, Yale University

Research Interests

Metal-catalyzed organic reaction development and mechanistic study

Research in the Shaughnessy group focuses on organometallic chemistry. One of the most interesting and important applications of organometallic complexes is as catalysts in organic synthesis. Therefore our efforts are focused on understanding organometallic reaction mechanisms that are relevant to important catalytic systems. By understanding the mechanism by which organometallic species catalyze important transformations, we can develop new or improved synthetic methodologies. Much of our research focuses on the use of alternative solvents in catalysis in an effort to develop more environmentally benign catalytic processes. Current research efforts in the group include the following:

  • Development of novel ligands for aqueous-phase catalysis: Water is an attractive environmentally benign solvent. We are interested in designing new ligands that will provide efficient, water-soluble catalysts for organic reactions. We have developed a family of water-soluble phosphines that provide efficient catalysts for palladium-catalyzed cross-coupling reactions in aqueous-solvents. Current efforts are focused at understanding the coordination chemistry of these ligands and designing the next generation of ligands that will provide improved catalyst performance.
  • Structure-activity relationships for ligands: The Shaughnessy group has a long-standing interest in understanding how steric and electronic properties of ligands affect catalyst performance.  In collaboration with computational chemists, we try to understand how ligand design can be used to design more efficient catalyst systems.

Students in the Shaughnessy group gain experience in a wide range of synthetic techniques for organic and organometallic synthesis as well as experience with a variety of spectroscopic techniques (i.e., NMR, IR, UV/Visible, and Mass spectroscopy, as well as X-ray crystallography).

Representative Publications

“Kinetic Analysis of Aqueous-Phase Pd-Catalyzed, Cu-Free Direct Arylation of Terminal Alkynes Using a Hydrophilic Ligand,” Hartman, R. L.; Moore, J. N.; Domier, R. C.; Shaughnessy, K. H. Org. Proc. Res. Dev., 2013, 17, 1262-1271.

“Trineopentylphosphine: A Conformationally Flexible Ligand for the Coupling of Sterically Demanding Substrates in the Buchwald-Hartwig Amination and Suzuki-Miyaura Reaction,” Raders, S. M.; Moore, J. N.; Parks, J. K.; Miller, A. D.; Leißing, T. M.; Kelley, S. P.; Rogers, R. D.; Shaughnessy, K. H., J. Org. Chem., 2013, 78, 4649-4664.

“Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides,” Dolliver, D. D.; Bhattarai, B. T.;  Pandey, A.; Lanier, M. L.; Bordelon, A. S.; Adhikari, S.; Dinser, J. A.; Flowers, P. F.; Wills, V. S.; Schneider, C. L.; Shaughnessy, K. H.; Moore, J. N.; Raders, S. M.; Snowden, T. S.; McKim, A. S.; Fronczek, F. R., J. Org. Chem, 2013, 78, 3676-3687.

“Aqueous-Phase Heck Coupling of 5-Iodouridine and Alkenes under Phosphine-Free Conditions.” Cho, J. H.; Shaughnessy, K. H. Synlett 2011, 2963-2966.

“Synthesis and X-ray Structure Determination of Highly Active Pd(II), Pd(I), and Pd(0) Complexes of Di(tert-butyl)neopentylphosphine (DTBNpP) in the Arylation of Amines and Ketones,” Hill, L. L.; Crowell, J. L.; Tutwiler, S. L., Massie, N. L., Hines, C. C.; Griffin, S. T.; Rogers, R. D.; Shaughnessy, K. H.; Grasa, G. A.; Johansson Seechurn, C. C. C.; Li, H.; Colacot, T. J.; Chou, J.; Woltermann, C. J. J. Org. Chem. 2010, 75, 6477-6488.

“Efficient Sonogashira Coupling of Unprotected Halonucleosides in Aqueous Solvents Using Water-Soluble Palladium Catalysts,” Cho, J. H.; Prickett, C. D.; Shaughnessy, K. H. Eur. J. Org. Chem. 2010, 3678-3683.

“Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions,” Shaughnessy, K. H. Chem. Rev., 2009, 109, 643-710.

“Sterically-Demanding, Zwitterionic Trialkylphosphonium Sulfonates as Air-Stable Ligand Precursors for Efficient Palladium-Catalyzed Cross-Couplings of Aryl Bromides and Chlorides,” Brown, W. S.; Boykin, D. D.; Sonnier, M. Q., Jr.; Clark, W. D.; Brown, F. V.; Shaughnessy, K. H. Synthesis, 2008, 1965-1970.

“Neopentylphosphines as Effective Ligands in Palladium-Catalyzed Cross-Couplings of Aryl Bromides and Chlorides,” Hill, L. L.; Smith, J. M.; Brown, W. S.; Moore, L. R.; Guevara, P.: Pair, E. S.; Porter, J.; Chou, J.; Wolterman, C. J.; Craciun, R.; Dixon, D. A.; Shaughnessy, K. H. Tetrahedron, 200864, 6920-6934.

“Sterically Demanding, Sulfonated, Triarylphosphines:  Application to Palladium-Catalyzed Cross-Coupling, Steric and Electronic Properties, and Coordination Chemistry,” Moore, L. R.; Western, E. C.; Craciun, R.; Spruell, J. M.; Dixon, D. A.; O’Halloran, K. P.; Shaughnessy, K. H. Organometallics, 200827, 576-593.