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Mary P. Watson, Ph.D., University of Delaware, Department of Chemistry
Title: Stereospecific, Nickel-Catalyzed Cross Couplings of Alkyl Electrophiles
Transition metal-catalyzed cross coupling reactions have revolutionized organic synthesis, particularly the construction of bonds to sp2-hybridized carbons. However, the discovery of analogous reactions of Csp3 electrophiles have lagged behind, despite their potential to deliver a range of important targets, including chiral molecules in high enantiopurity. In particular, di- and tri-aryl alkanes are important molecules in organic synthesis. Stereospecific cross couplings of benzylic electrophiles with organometallic reagents provide a highly efficient and powerful route to these molecules, particularly if the benzylic electrophiles can be prepared in exceptional enantiopurity. To this end, we have developed stereospecific, nickel-catalyzed cross couplings of both benzylic amine and benzylic alcohol derivatives. These reactions proceed with high levels of stereochemical fidelity; employ air-stable, functional group tolerance coupling partners, such as aryl boronic acids; and display excellent functional group tolerance. This strategy is also effective for the arylation of allylic electrophiles, and the use of alternative coupling partners. The optimization, scope, and mechanistic studies of these reactions will be presented.
Mary P. Watson was born in Massachusetts in 1977 and grew up in Tampa, FL. She completed an A.B. in Chemistry at Harvard University in 2000. During college, she performed undergraduate research with Prof. David A. Evans at Harvard, as well as with Prof. Kenneth B. Wagener at the University of Florida.
Under the direction of Prof. Larry E. Overman, she earned a Ph.D. in organic chemistry in 2006 from the University of California, Irvine. Her doctoral thesis focused on the development and mechanistic investigation of the palladium(II)-catalyzed asymmetric allylic imidate rearrangement. During the course of this work, she had the opportunity to collaborate with Prof. Robert G. Bergman at the University of California, Berkeley, where she performed kinetic and computational studies.
From 2006–2009, she was a National Institutes of Health NRSA postdoctoral fellow at Harvard University in Professor Eric N. Jacobsen’s research group. During her postdoc, she developed a nickel-catalyzed method for olefin arylcyanation via activation of C–CN bonds.
In July 2009 she joined the faculty at the University of Delaware, and she was promoted to Associate Professor in 2016. Her research group is working to develop new catalytic methods for the synthesis of organic molecules. In particular, they utilize transition metal catalysts to efficiently prepare highly enantioenriched products. Her research has received generously support from the University of Delaware Research Foundation, the American Chemical Society Petroleum Research Fund, the National Institutes of Health (R01 and COBRE programs), and the National Science Foundation (Early Career Award). The impact of her research program has been recognized with a Rising Star award from the Women Chemists’ Committee of the American Chemical Society and a Thieme Chemistry Journal Award. Mary and her husband are also proud parents of 3.5 year old twin girls.
*Please specify a choice of entrée, vegetarian entrée by request
Price: $25.00 (includes social hour); $15 for students and retirees
Date: Thursday, October 20, 2016
Time: 5:30-social hour (Science Center Lobby)
6:15-dinner/business meeting (Science Center Lobby)
7:30-speaker (Science Center Lecture Hall)
Place: Albright College
Directions: To campus: http://www.albright.edu/about/directions.html
Campus map: http://www.albright.edu/about/Printable-Map.pdf
Contact: Reservations by 4:00 P.M. Thursday, October 13, 2016 through
Pam Artz: (610) 921-7741; email@example.com
(E-mail is preferred with LVACS as the subject). Please specify a choice of entrée and any dietary restrictions.