Publications

Student Theses and Dissertations

Publications at UA

  1. "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..
  2. " 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
  3. "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.
  4. "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.
  5. "Aqueous-Phase Heck Coupling of 5-Iodouridine and Alkenes under Phosphine-Free Conditions." Cho, J. H.; Shaughnessy, K. H. Synlett 2011, 2963-2966.
  6. "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.
  7. "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.
  8. "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.
  9. "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.
  10. "A General Synthesis of C8-Arylpurine Phosphoramidites," Vongsutilers, V.; Daft, J. R.; Shaughnessy, K. H.; Gannett, P. M. Molecules, 2009, 14, 3339-3352.
  11. "Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions," Shaughnessy, K. H. Chem. Rev, 2009, 109,643-710.
  12. "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
  13. "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
  14. "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.
  15. "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.
  16. "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.
  17. "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
  18. "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
  19. "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.
  20. "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
  21. "Inhibitory Effects of the Guanine Moiety on Suzuki Couplings of Unprotected Halonucleosides in Aqueous Media," Western, E. C.; Shaughnessy, K. H., J. Org. Chem., 2005, 70, 3678-3688.
    Supporting Information
  22. "Palladium-Catalyzed Hydroesterification of Styrene Derivatives in the Presence of Ionic Liquids," Klingshirn, M. A.; Rogers, R. D.; Shaughnessy, K. H. J. Organomet. Chem. 2005, 690, 3620-3626.
    • Special Ionic Liquids Issue
    • #25 most downloaded article for 3rd quarter of 2005
  23. "Kinetic Study of the Oxidative Addition of Methyl Iodide to Vaska's Complex in Ionic Liquids," P'Pool, S. J.; Klingshirn, M. A.; Rogers, R. D.; and Shaughnessy, K. H. J. Organomet. Chem. 2005, 690, 3522-3528.
    • Special issue on Ionic Liquids
  24. "Promoting Effect of Ionic Liquids on Ligand Substitution Reactions." Sliger, M. D.; Traylor, R. K.; McNeill, J., III; Young, S. H.; Hoffman, N. W.; Klingshirn, M. A.; Rogers, R. D.; and Shaughnessy, K. H. J. Organomet. Chem. 2005, 690, 3540-3545.
    • Special issue on Ionic Liquids
  25. "Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications." Shaughnessy, K. H.; DeVasher, R. B. Curr. Org. Chem. 2005, 9(7), 585-604.
    • Invited review for a special issue on modern transition-metal catalyzed reactions.
  26. "Di-t-butyl(ferrocenylmethyl)phosphine: air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions." Sliger, M. D.; Shaughnessy, K. H.; Broker, G. A.; Griffin, S. T.; Rogers, R. D. J. Organomet. Chem., 2005, 690, 1478-1486.
    • #7 most downloaded article for the 1st quarter of 2005
    • Top 25 download from JOMC for 2005
  27. "Experimental and Computational Study of Steric and Electronic Effects on the Coordination of Sterically Demanding, Water-Soluble Alkylphosphines to Palladium under Reducing Conditions: Correlation to Catalytic Activity." DeVasher, R. B.; Spruell, J. M.; Dixon, D. A.; Broker, G. A.; Griffin, S. T.; Rogers, R. D.; Shaughnessy, K. H. Organometallics, 2005, 24, 962-971.
    Supporting information
  28. "Aqueous-Phase, Palladium-Catalyzed Cross-Couplings of Aryl Bromides Under Mild Conditions Using Water-Soluble, Sterically Demanding Alkylphosphines." DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919-7927.
    Supporting information
  29. "Efficient aqueous-phase Heck and Suzuki couplings of aryl bromides using tri(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt (TXPTS)." Moore, L. R. and Shaughnessy, K. H. Org. Lett. 2004, 6, 225-228.
    Supporting information
  30. Synthesis, Properties and NMR Studies of a C8-Phenylguanine Modified Oligonucleotide that Preferentially Adopts the Z-DNA Conformation.” Gannett, P. M.; Heavner, S.; Daft, J. R. Shaughnessy, K. H.; Epperson, J. D.; Greenbaum, N. L. Chem. Res. Tox. 2003, 16, 1384-1395.
  31. Efficient One-Step Suzuki Arylation of Unprotected Halonucleosides using Water-Soluble Palladium Catalysts,” Western, E. C.; Daft, J. R.; Johnson, E. M., II; Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem., 2003, 68, 6767-6774.
    Supporting information
  32. "Polar, Non-Coordinating Ionic Liquids as Solvents for Coordination Polymerization of Olefins," Shaughnessy, K.H.; Klingshirn, M. A.; P'Pool, S. J.; Holbrey, J. D.; Rogers, R. D. ACS Symposium Series 856: Ionic Liquid as Green Solvents: Progress and Prospects, Rogers, R. D.; Seddon, K. R. (Eds), American Chemical Society, Washington, DC, 2003, 300-313.
  33. "Acid-Mediated, Chromium-Catalyzed Allylation of Aldehydes," K. H. Shaughnessy and R. Huang, Synth. Comm., 2002, 32, 1923-1928.
  34. "Polar, Non-Coordinating Ionic Liquids as Solvents for the Alternating Copolymerization of Styrene and CO Catalyzed by Cationic Palladium Catalysts." Klingshirn,M. A.; Broker G. A.; Holbrey, J. D.; Rogers, R. D.; and Shaughnessy, K. H. Chem. Commun. 2002, 1394-1395.
    Supporting information
  35. "Sterically Demanding, Water-Soluble Alkylphosphines as Ligands for High Activity Suzuki Couplings in Aqueous Solvents" Shaughnessy, K. H. and Booth, R. S. Org. Lett., 2001, 3 2757-2759.
    Supporting information

Books and Book Chapters at UA

  1. Shaughnessy, K. H. "Cross-Coupling Reactions in Aqueous Media," in Palladium-Catalyzed Cross-Coupling Reactions - Practical Aspects  and Future Developments, Molnár, Á. Ed., Wiley-VCH, 2013, pp 235-286.  ISBN: 978-3-527-33254-0
  2. Shaughnessy, K. H. "Metal-Catalyzed Cross-Couplings of Aryl Halides to Form C–C Bonds in Aqueous Media," in Metal-Catalyzed Reactions in Water, Diexnuf, P.; Cadierno, V. Eds., Wiley-VCH, 2013, pp 1-46.  ISBN: 978-3-527-33188-8

Published Abstracts and Non-Peer-Reviewed Publications at UA

  1. "1-Trimethylammonium-2-(di-t-butyl)phosphino)ethane chloride, t-Bu-Amphos," Shaughnessy, K. H. Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS), published online April 22, 2013
  2. Sayler, F. M.; Grano, A. J.; Scogin, W.; Sanders, P.; Smått, J.-H.; Shaughnessy, K. H.; Bakker, M. G. "Formation and Applications of Hierarchically Porous Carbon, Metals and Metal Oxides Formed by Nanocasting",  MRS Symp. Proc., 2012, 1389, 1-8.
  3. "Bis(1,1-dimethylethyl)2,2-dimethylpropylphosphine," Shaughnessy, K. H. Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS), published online October 15, 2010
  4. "2-(Pentafluorophenyl)-1,3-bis(2,4,6-trimethylphenyl)-imidazolidine," Shaughnessy, K. H. Electronic Encyclopedia of Reagents for Organic Synthesis (eEros), 2008, published online September 15th, 2008.
  5. "Tri-tert-butylphosphonium tetrafluoroborate," Shaughnessy, K. H. Electronic Encyclopedia of Reagents for Organic Synthesis (eEros), 2008, published online March 14th, 2008.
  6. Palladium, bis(tris-(1,1-dimethylethyl)phosphine,” Shaughnessy, K. H. Electronic Encyclopedia of Reagents for Organic Synthesis (eEros), 2008, published online March 14th, 2008.
  7. "On Comprehensive Organic Reactions in Aqueous Media by Chao-Jun Li and Tak-Hang Chan" Shaughnessy, K. H. " Angew. Chem. Int. Ed. 2008, 47, 1988. (Book Review)
  8. "Tri-tert-butylphosphine," Shaughnessy, K. H. Electronic Encyclopedia of Reagents for Organic Synthesis (eEros), 2007, published online March 15th, 2007.
  9. "Coordination Polymerization of Alkenes in Ionic Liquids." Shaughnessy, K. H.; P'Pool, S. J.; Klingshirn, M. A.; Rogers, R. D. Polymer Prepr. 2004, 45, 317-318.
  10. "Transition Metal Catalyzed CO/Olefin Co-Polymerization in Room Temperature Ionic Liquids," Holbrey, J. D.; Shaughnessy, K. H.; Klinshirn, M. A.; Broker, G. A.; Rogers, R. D. in Molten Salts XIII, Delong, H. C.; Bradshaw, R. W.; Matsunaga, M.; Stafford, G. R.; Trulove, P. C. Eds. 2002, 2002-19, pp 213-223, The Electrochemical Society Proceedings Series, Pennington, NJ.

Post-Doctoral Publications

  1. "Screening of Homogeneous Catalysts by Fluorescence Resonance Energy Transfer. Identification of Catalysts for Room Temperature Heck Reactions," J. P. Stambuli, S. R. Stauffer, K. H. Shaughnessy, J. F. Hartwig, J. Am. Chem. Soc., 2001, 123, 2677-2678.
  2. "Room Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C-N Bond Formation with a Commercial Ligand." J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem., 1999, 64, 5575-5580.
  3. "A Fluorescence Assay for High-Throughput Screening of Coupling Reactions. Application to Heck Coupling Processes." K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2131.
  4. "Palladium Catalyzed Inter-and Intramolecular a-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles." K. H. Shaughnessy, B. C. Hamann, J. F. Hartwig, J. Org. Chem., 1998, 63, 6546-6553.
  5. "Transition metal-catalyzed process or preparing N-aryl compounds," J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman (Yale University), US Patent 6,100,398 (2000)

Graduate Publications

  1. "Enantio- and Diastereoselective Catalytic Carboalumination of 1-Alkenes and α,ω-Dienes with Cationic Zirconocenes: Scope and Mechanism." K. H. Shaughnessy and R. M. Waymouth, Organometallics, 1998, 17, 5728-5745.
  2. "Highly Regioselective Cyclocarboxylation of Nonconjugated Dienes Catalyzed by Palladium." K. H. Shaughnessy and R. M. Waymouth, Organometallics, 1997, 16, 1001-1007.
  3. "Carbometalation of α,ω-Dienes and Olefins Catalyzed by Zirconocenes." K. H. Shaughnessy and R. M. Waymouth, J. Am. Chem. Soc. 1995, 117, 5873-5874.

Undergraduate Publications

  1. "A Facile Method for the Preparation of Functionalized 2-Halo-1-olefins." Zhu, L.; Shaughnessy, K. H.; Rieke, R. D. Synth. Comm., 1993, 23, 525-529.

Links to papers above will direct you to the appropriate DOI page. Articles are available for download with subscription, or may be purchased individually from the publisher.

Last updated October 30, 2013

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

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