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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. We are particularly interested in the design of ligands to promote interesting metal-catalyzed transformations. Our efforts in ligand design focus on trying to understand the role of steric and electronic ligand properties on catalytic processes. Another area of general interest is the design of sustainable metal-catalyzed synthetic processes. Areas of current interest include:
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).
"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, 4649-4664.
"Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of N-Alkoxyimidoyl Iodides and Bromides," Dolliver, D. D.; Bhattarai, B.; 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, 3676-3687.
"Aqueous-phase Sonogashira alkynylation to synthesize 5-substituted pyrimidine and 8-substituted purine nucleosides," Cho, J. H.; Shaughnessy, K. H. Curr. Prot. Nucleic Acid Chem. 2012, 49, 1.27.1-10.
"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, 64, 6920-6934 (2008)
"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, 27, 576-593 (2008).
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