18th Biannual: John Eisch Lectureship In
Organic Chemistry
Thursday, February 6, 2025
4 P.M.
Smart Energy Building, Fountain Room
Professor Melanie Sanford
Moses Gomberg Distinguished
University Professor of Chemistry
and Arthur F. Thurnau Professor
Department of Chemistry
University of Michigan
Development of Metal-Catalyzed Reactions for Introducing Fluorine Into Organic Molecules
This presentation will describe our group’s recent advances in developing metal-mediated/catalyzed methods for introducing fluorine into organic molecules. Our efforts into this area are guided by detailed fundamental studies of stoichiometric organometallic bond-forming reactions. These fundamental studies will be described in detail, and their translation to practical applications (particularly in the context of the synthesis of PET imaging agents) will be discussed
- Information about Professor Melanie Sanford
Melanie S. Sanford is currently the Moses Gomberg Distinguished University Professor of Chemistry and Arthur F. Thurnau Professor of Chemistry at the University of Michigan, Ann Arbor. She received her BS and MS degrees at Yale University in 1996, where she carried out undergraduate research in the laboratory of Professor Robert Crabtree. She pursued graduate studies at the California Institute of Technology, working with Professor Robert Grubbs. Following postdoctoral work at Princeton University with Professor John Groves, she joined the faculty at the University of Michigan in the summer of 2003 as an assistant professor of chemistry. She was promoted to associate professor in 2007, to full professor in 2010, to Arthur F. Thurnau Professor of Chemistry in 2011, and to Moses Gomberg Distinguished University Professor of Chemistry in 2016.
Professor Sanford has won a number of awards, including the ACS Award in Pure Chemistry, the Sackler Prize, the Blavatnik Award, a MacArthur Foundation Fellowship, and the ACS Award in Organometallic Chemistry. She is a member of the National Academy of Sciences, the American Academy of Arts and Sciences, and a Fellow of the ACS. She has trained close to 100 graduate students and post-docs. Research in the Sanford group aims to develop new chemical reactions that enable the production of pharmaceuticals, agrochemicals and fuels in a more efficient and environmentally friendly manner. For example, her research focuses on converting simple and readily available starting materials (e.g. carbon-hydrogen bonds, carboxylic acid derivatives) into much more complex products using transition metal catalysis.
- Information about Professor John J. Eisch
John Joseph Eisch joined the Department of Chemistry at Binghamton University in 1972, as chair and professor of chemistry, with the mandate of fostering the national reputation of its graduate teaching and research. Over the next six years as chair, he guided the recruiting of six senior and junior faculty with this goal in mind, while expanding his own research in organometallic chemistry to a yearly group of eight to 12 graduate and postdoctoral students, with support from federal and industrial resources. In 1983, his composite achievements were recognized by his promotion to the SUNY-wide rank of distinguished professor of chemistry. Further recruiting, notably during the chair tenure of professors Eugene Stevens, Alistair Lees, Wayne Jones and currently, Eriks Rozners, expanded the scope of advanced research into areas of immediate importance, such as nano materials, homogeneous catalysis, analytical sensors, biological transformations and energy storage.
Eisch received the BS degree in chemistry, summa cum laude, from Marquette University in 1952; earned the PhD degree in 1956, with Henry Gilman, at Iowa State University; and served as Union Carbide Research Fellow with Karl Ziegler at the Max-Planck-Institut für Kohlenforschung, Mülheim, Germany (1956–57). After junior professional appointments at St. Louis University and the University of Michigan, he became ordinary professor and department head at the Catholic University of America (1963–1972). He retired from his professorial career of 57 years in 2014, the latter 42 years of which were spent at Binghamton University.
The Eisch Group initially had concentrated on the preparation and organic synthetic uses of organometallic reagents of Li, Na, Mg, B and Al, but we were struck by the lack of definitive molecular mechanistic studies in previous work. In ensuing research encompassing reaction kinetics, trapping of any intermediates, IR, UV and X-ray crystallographic measurements, both heterolytic and homolytic C-M cleavages could be involved, as well as 4-centertrapesoidal transition states. Reviews are available in a) “Fifty Years of Ziegler- Natta Polymerization: From Serendipity to Science,” Organometallics, 2012, 31, 4917–4932 and b) Dalton Transactions, (DOI: 10:1039/c4dt010362) “Emergence of Electrophilic Alumination as the Counterpart of Established Nucleophilic Lithiation.” The original seven articles dealing with the reactions of RLi with the azomethyne groups have been recently published by the Eisch and the Rheingold Crystallographic Group in the European Journal of Organic Chemistry.
Over the years, the research involved the fruitful collaboration of more than 200 students as master’s, doctoral, postdoctoral or baccalaureate associates. The results have been reported in more than 410 scientific publications, in some 280 invited lectures worldwide, in the monograph “The Chemistry of Organometallic Compounds” (Macmillian, 1967) and in the edited series, “Organometallic Syntheses” (four volumes, J. J. Eisch and R. B. King, authors and editors). He has been an industrial consultant on organometallic chemistry and an expert witness in several patent litigations on Ziegler-Natta polymerization catalysis.
One of the significant discoveries of our studies is that the reaction of organic carbanionic reagents is not a one-step nucleophilic C alpha attack (i) but a two-step electrontransfer and electron-coupling process (ii)(iii).
- Previous Lectureship Recipients
2012
Stephen L. Buchwald - MIT
“Palladium-Catalyzed CarbonNitrogen and Carbon-Carbon Bond-Forming Reactions: Progress, Applications and Mechanistic Studies”
2013
David W. C. MacMillan - Princeton University
“The Use of Photoredox Catalysis in New Organic Bond Forming Reactions”
2014
Brian M. Stoltz - California Institute of Technology
“Complex Natural Products as a Driving Force for Discovery in Organic Chemistry”
2015
Eric N. Jacobsen - Harvard University
“Anion-Binding Catalysis”
2016
Bob Crabtree - Yale University
“Organometallic Catalysis for Solar Fuels and Storage”Phil S. Baran - The Scripps Research Institute
“Translational Chemistry”
2017
Stephen J. Lippard - MIT
“Understanding and Improving Platinum Anticancer Drugs”Daniel A. Singleton - Texas A&M Uniersity
“Dynamic Effects and Energy Labeling in Free-Radical Reactions”
2018
Clifford P. Kubiak - University of California, San Diego
“If You Make a Solar Fuel From CO2, What Should It Be?”Scott E. Denmark - University of Illinois at Urbana-Champaign
"Lewis-base Activation of Lewis Acids: An Evolving Paradigm for Catalysis in Main Group Chemistry"
2019
Professor Gregory C. Fu - California Institute of Technology "Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Reactions"
John F. Hartwig - University of California, Berkeley
"Selective, Catalytic Functionalization of C-H Bonds with Small and Large Catalysts"
2021
Professor Vern L. Schramm - Albert Einstein College of Medicine
"Enzymatic Transition States and Transition State Analogues"
2022
Karen Goldberg - University of Pennsylvania
"Molecular Oxygen as a Reagent in Late Transition Metal Organometallic Chemistry"
2023
Kendall N. Houk - University of California, Los Angeles "Pericyclic Reactions: Theory, Mechanisms, Dynamics and Role in Biology"
Polly L. Arnold - University of California, Berkeley
"F-Block Dinitrogen Chemistry; from Rarity to Catalysis in a Few Simple Steps"
2024
Professor Gregory H. Robinson - University of Georgia
"N-Heterocyclic Carbenes and Dithiolene Radicals: Counterintuitive Main Group Chemistry"
