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Sunday, 13 December 2015

Kevin H. Shaughnessy

image file: BK9781849738965-FP021-u29.tif 
 Kevin H. Shaughnessy

Kevin H. Shaughnessy

Rm 2007 Shelby Hall
Ph: 205-348-4435
Fax: 205-348-9104
Department of Chemistry
Box 870336
The University of Alabama
Tuscaloosa, AL 35487-0336

Kevin H. Shaughnessy grew up in the small town of Trumbull, Nebraska. He earned his BS degree from the University of Nebraska–Lincoln in 1992, where he worked with Reuben D. Rieke. He then joined the group of Robert M. Waymouth at Stanford University, where he developed zirconocene-catalyzed carbometallation reactions. Upon completing his PhD degree in 1998, he moved to Yale University to work with John F. Hartwig on palladium-catalyzed enolate arylations and the development of high-throughput screening assays.

In 1999, he joined the Chemistry Faculty at the University of Alabama, where he is currently Professor and Chair of Chemistry. His research interests are focused on the development of catalytic methodologies in alternative solvents, design of new ligands, and mechanistic studies of ligand structure–activity relationship


Kevin H. Shaughnessy

Download complete CV (PDF) - updated 06/05/2013
Current Position Associate Professor (2005 - present)
Chair (2009-present)
Department of Chemistry
The University of Alabama
Box 870336
Tuscaloosa, AL 35487-0336
Phone (205) 348-4435
Fax: (205) 348-9104
Email Kevin Shaughnessy
Prior Positions
2007-2009: Director of Undergraduate Studies in Chemistry, The University of Alabama, Tuscaloosa, AL
1999-2005: Assistant Professor of Chemistry, The University of Alabama, Tuscaloosa, AL

Post-Doctoral Experience Yale University, New Haven, CT (1997 - 1999)
Advisor: Prof. John F. Hartwig
Palladium catalyzed coupling of aryl-halides and carbon and heteroatom nucleophiles. Development of high-throughput screening methodologies for determining catalytic activity
Education Ph.D., Organic Chemistry, Stanford University, Stanford, CA (1998)
Dissertation: Synthetic and Mechanistic Studies of Metal-Catalyzed Diene Cyclizations
Advisor: Prof. Robert M. Waymouth
B.S. with Honors and Distinction, Chemistry, University of Nebraska-Lincoln (1992)

Research Interests The mechanistic study of organometallic reactions involved in synthetically important catalytic cycles; metal-catalyzed cross-coupling, catalyst design for use in alternative solvents, green chemistry, metal-catalyzed biomolecule modification, development of new classes of bond activation and formation, biomass utilization.

Dr. Kevin Shaughnessy
  • 2007 Shelby Hall
  • (205) 348-4435
  • (205) 348-9104
Kevin Shaughnessy
Professor / Department Chair
2007 Shelby Hall Shaughnessy Group
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
Moore, J. N.; Laskay, N. M.; Duque, K. S.; Kelley, S. P.; Rogers, R. D.; Shaughnessy, K. H. “Synthesis of 4-Sulfonatobenzylphosphines and Their Application in Aqueous-Phase Palladium-Catalyzed Cross-Coupling,” J. Organomet. Chem. 2015, 777, 16-24.
Lauer, M. G.; Thompson, M. K.; Shaughnessy, K. H. “Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands,” J. Org. Chem., 2014, 79, 10837-10848.
Raders, S. M.; Jones, J. M.; Semmes, J. G.; Kelley, S. P.; Rogers, R. D; Shaughnessy, K. H. “Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones,” Eur. J. Org. Chem. 2014, 7395-7404.
Bhattarai, B. T. Adhikari, S.; Kimball, E. A.; Moore, J. N.; Shaughnessy, K. H.; Snowden, T. S.; Fronczek, F. R.; Dolliver, D. D. “Palladium-catalyzed ortho-halogenation of diaryl oxime ethers,” Tetrahedron Lett. 2014, 55, 4801-4806.
“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.
“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, 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.


Shaughnessy Group, April 2013. (l to r): Dayne Fraser, Kevin Duque, Luke Brechtelsbauer, Nick Laskay, Kevin Shaughnessy, Jessica Jones, Jeff Semmes, Stephanie Bevans, Mallory Thompson, Nigel Welch, Jane Moore

Group News

More Shaughnessy Group News
Congratulations Scott: Scott Brown defended his PhD dissertation and graduated in the August commencement ceremony. Scott has accepted a position as assistant professor at Murray State University in Kentucky.
New Students: Jordan Entrekin, Jackie Parks, Joseph Randall, and Austin Doss joined the group as undergraduate researchers this summer. They were joined by Cody Corbin who was an REU student from UAB. Jane Moore rejoined the group as an incoming graduate student after completing her degree at Tennessee Wesleyan University. Jane was an REU student in the group last summer.
Congratulations Graduates: Dr. Lensey Hill received her PhD degree in the May Commencement ceremony. Undergraduate researchers Dana Suich, Denise Boykin, Jason Crowell, Joel Schoenberg, Sarabeth McLendon, and Tyler James received their degrees as well. Congratulations to all and good luck in the future.
University System Honors Research Conference: Emily Wayman took first place in the Physical Sciences division of the University System Honors Undergraduate Research Conference. Emily is working on a joint project with the Shaughnessy and Dixon groups.
UA Undergraduate Research Conference: Group members took first and third place in the Natural Sciences division of the UA Undergraduate Research Conference Poster competition. Joel Schoenberg placed first with his poster entitled, "Palladium-Catalyzed Hydrodehalogenation of Aryl Bromides and Chlorides," and Duncan Harmon earned 3rd place with his poster entitled, "Synthesis and Characterization of Neopentylphosphine Palladium Complexes."
Alabama Academy of Science: Hannah Box placed first in the Chemistry division of the undergraduate poster competition at the AAS meeting. Hannah's poster was entitled, "Synthesis of Water-Soluble Phosphines and Their Application to Recyclable, Aqueous-Phase Palladium Catalyts."
GSE Inductee: Undergraduate researcher Duncan Harmon was one of 19 student inducted into Gamma Sigma Epsilon National Chemistry Honorary.
Hollings Scholarship: Undergraduate research student Emily Wayman has won an Ernest F. Hollings Undergraduate Scholarship from the National Oceanographic and Atmospheric Administration (NOAA).
Joseph and Bessie Mae Pryor Award: Jane Moore received the Joseph and Bessie Mae Pryor Award for her presentation at the Alpha Chi National Honor Society National Meeting in Indianapolis. Jane presented her work from last summer while in the group as an SURP participant.
Chemical Review Paper: An invited by review by Kevin Shaughnessy entitled, " Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions," has been published online by Chemical Reviews.
New Group Members: Nigel Welch and Dayne Fraser have joined the Shaughnessy group as graduate students. Nigel spent the summer with the group and came to UA from UT-Chattanooga. Dayne came to UA after earning his degree at Kennesaw State University in Atlanta. Also joining the group for the spring 2009 semester are undergraduate researchers Jared Carpenter, Duncan Harmon, and Dana Suich.
Graduates: Undergraduate researchers Fallon Brown and Quentin Sonnier received degrees in the Winter Commencement ceremony. Congratulations to both and thanks for their contributions to the group.
New Students: Zack Hawkins joined the group this fall. Zack is a freshman and a participant in the Emerging Scholars Program.
Lensey Defends: Lensey Hill successfully defended her dissertation on November 10th. Lensey has turned in her dissertation and started a job with Georgia Pacific. She will officially graduate in May 2009.
NSF Organometallic Catalysis Workshop: Lensey Hill was chosen to attend the NSF-sponsored 2008 CENTC Summer School on Organometallic Catalysis at the University of Washington.
Papers published: Two group papers recently appeared in print. A paper describing C-Se bond formation co-authored by Joon Cho and Fallon Brown was published recently in Main Group Chemistry (Main Group Chem. 2007, 6, 201-214) . A paper on new water-soluble phosphines was published in a special issue of Synthesis focused on aqueous-phase catalysis (Synthesis, 2008, 1965-1970) . Co-authors on this paper were Scott Brown, Denise Boykin, Quentin Sonnier, William Clark, and Fallon Brown.
ACS Scholar: Denise Boykin has recipient of a scholarship for the 2008-09 school year from the ACS Scholars Program. This American Chemical Society program provides scholarships for students from underrepresented minorities pursuing degrees in the chemical sciences or chemical technology.
New Students: Joel Schoenberg, Tyler James, Jane Moore, Hannah Box, Emily Wayman, and Nigel Welch joined the group this summer. Joel, Tyler, Hannah and Emily are UA undergraduates. Jane is a participant in the UA SURP program from Tennessee Wesleyan. Nigel is an incoming graduate student who received his undergraduate degree from UT-Chattanooga.
Graduates: Congratulations to the group members who earned degrees during the May commencement. Paul Guevara (cum laude), Ellie Killian, Nick Massie (summa cum laude), and Strud Tutwiler (magna cum laude) all earned BS degrees in chemistry.
Phi Beta Kappa: Undergraduate researchers Fallon Brown, Nick Massie, and Strud Tutwiler were inducted into Phi Beta Kappa during the 2007-2008 academic year. Congratulations for being inducted into the oldest and most prestigious academic honor society.
A&S Distinguished Undergraduate Scholar: Nick Massie was a recipient of the Distinguished A&S Undergraduate Scholar award presented during Honors Week.
Randall Outstanding Undergraduate Research Award: Denise Boykin was one of 18 students to receive the Randall Outstanding Undergraduate Research Award during Honors Week. Denise was one of 6 chemistry majors recognized for their outstanding contributions to research at UA.
Spring ACS Meeting: The Shaughnessy group presented 8 papers at the National ACS meeting in New Orleans. Presenting authors were, Scott Brown, Lensey Hill, Denise Boykin, Fallon Brown, Sarabeth McLendon, Ellie Killian, Quentin Sonnier, Strud Tutwiler, and Jason Crowell.
AAS Meeting: Quentin Sonnier won the first prize in the Alabama Academy of Science undergraduate paper competition at the annual meeting at Samford University. Lensey Hill placed second in the poster competition.
Neopentylphosphine paper: A paper co-authored by Lensey L. Hill, Joanna M. Smith, William S. Brown, Lucas R. Moore, Paul Guevera, Emily S. Pair, Jake Porter, Joe Chou, Christopher J. Wolterman, Raluca Craciun, David A. Dixon and Kevin H. Shaughnessy on the use of neopentylphosphines in cross-coupling reactions has been published online by Tetrahedron (Tetrahedron, 2008, 64, 6920-6934) This paper is being published in a special issue of Tetrahedron honoring John Hartwig.
TXPTS paper published: A paper co-authored by Lucas Moore, Beth Western, Kevin O'Halloran, Raluca Craciun, Jason Spruell, and David Dixon on the catalytic application, properties, and coordination chemistry of the TXPTS ligand has been published in Organometallics.
New group members: William Clark and Nick Massie have joined the group as undergraduate researchers.
Graduation: Dr. Joon Cho formally earned his PhD degree in the December commencement ceremony. Former undergraduate reserach Jake Porter received a BS degree in chemistry.
Distinguished Teaching Fellow: Kevin Shaughnessy has been named an Arts & Sciences Distinguished Teaching Fellow for the period 2007-2010 by Dean Olin.
Dental School: Undergraduate research Strud Tutwiler has been accepted to UA School of Dentistry for the fall 2008 semester. Congrats, Strud!
OCTA Award: Kevin Shaughnessy has been named a 2007 recipient of the Outstanding Commitment to Teaching Award, which is given each year by the National Alumni Association to four faculty members at UA. The OCTA award is the highest teaching award given to UA faculty.
New Group Members: Sara McLendon, Jason Crowell, and Ellie Killian joined the group this fall as undergraduate researchers.

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



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