Shaughnessy, Kevin - The University of Alabama

个人简介

Education: Undergraduate Degree BS, 1992, University of Nebraska Education: Doctoral Degree Ph.D., 1998, Stanford University Education: Other Postdoctoral Associate, 1997-1999, Yale University

研究领域

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).

近期论文

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"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, 4649-4664. Featured Article "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. "The Conformational Effect of para-Substituted C8-Arylguanine Adducts on the B/Z/-DNA Equilibrium," Vongsutilers, V.; Phillips, D. J.; Train, B. C.; McKelvey, G. R.; Thomsen, N. M.; Shaughnessy, K. H.; Lewis, J. P.; Gannett, P. M. Biophys. Chem., 2011, 154, 41-48. "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. "Prediction of Reliable Metal–PH3 Bond Energies for Ni, Pd, and Pt in the 0 and +2 Oxidation States" Craciun, R.; Vincent, A. J.; Shaughnessy, K. H.; Dixon, D. A. Inorg. Chem., 2010, 49, 5546-5553. "A General Synthesis of C8-Arylpurine Phosphoramidites," Vongsutilers, V.; Daft, J. R.; Shaughnessy, K. H.; Gannett, P. M. Molecules, 2009, 14, 3339-3352. "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. Invited manuscript "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. J.; Pair, E. S.; Porter, J. E.; Chou, J.; Woltermann, C. J.; Craciun, R.; Dixon, D. A.; Shaughnessy, K. H. Tetrahedron, 2008, 64, 6920-6934. Invited Symposium in Print manuscript "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, 2008, 27, 576-593. "A Selective and Tin-Free Pd-Catalyzed Phenylselenylation of Aryl Bromides" Cho, J. H.; Brown, F. V.; Shaughnessy, K. H. Main Group Chem. 2007, 7, 210-214. Invited symposium paper. "Synthesis and Characterization of Water-Soluble Silver and Palladium Imidazol-2-ylidene Complexes with Non-Coordinated Anionic Substituents, " Moore, L. R.; Cooks, S. M; Anderson, M. S.; Schanz, H.-J.; Griffin, S. T.; Rogers, R. D.; Kirk, M. C; Shaughnessy, K. H. Organometallics, 2006, 25, 5151-5158. "Water-Soluble Palladacycles as Precursors to Highly Recyclable Catalysts for the Suzuki Coupling of Aryl Bromides in Aqueous Solvents," Huang, R. and Shaughnessy, K. H. Organometallics, 2006, 25, 4105-4112. Supporting information #2 most accessed article for July-September 2006 "Bulky Alkylphosphines with Neopentyl Substituents as Ligands in the Amination of Aryl Bromides and Chlorides," Hill, L. L.; Moore, L. R.; Huang, R.; Craciun, R.; Vincent, A. J.; Dixon, D. A.; Chou, J.; Woltermann, C. J.; Shaughnessy, K. H. J. Org. Chem., 2006, 71, 5117-5125. Supporting information "Beyond TPPTS: New Approaches to the Development of Efficient Palladium-Catalyzed Aqueous-Phase Cross-Coupling Reactions," Kevin H. Shaughnessy, Eur. J. Org. Chem., 2006, 1827-1835. Cover Artwork. Invited review. Top 10 most downloaded article in March and April 2006. "t-Bu-Amphos-RhCl3•3H2O: A Highly Recyclable Catalyst System for the Cross-Coupling of Aldehydes and Aryl- and Vinylboronic Acids in Aqueous Solvents," Huang, R.; Shaughnessy, K. H., Chem. Commun., 2005, 4484-4486. Supporting Information