Design and Applications of Selective Metathesis Catalysts
Thursday, April 18th, 2013
12:45 PM Room 1093 Shelby Hall
Bugs, Windmills, and Victoria’s Secret: Fundamental Science to Commercial Products
Friday, April 19th, 2013
3:30 PM, Room 1004 Shelby Hall
(General Audience Lecture)
Professor Grubbs’ visit was cosponsored by the College of Arts & Sciences Leadership Board Nobel Lectureship.
Professor Robert H. Grubbs is Victor and Elizabeth Atkins Professor of Chemistry at the California Institute of Technology, Pasadena, CA. Born in February 1942, Robert was raised in Kentucky between the towns of Calvert City and Possum Trot. He obtained his B.S. degree (1963) and M.S. degree (1965) under the direction of Professor Merle Battiste at the University of Florida. In 1965, Robert moved to Columbia University to conduct doctoral research with Professor Ronald Breslow. After earning his PhD in 1968, Robert worked as an NIH Postdoctoral Fellow for one year with Professor James. P. Collman at Stanford. Robert started his independent research career at Michigan State in 1969, where he earned early promotion to Associate Professor of Chemistry. In 1978, Robert was lured from East Lansing to Pasadena. He and his wife Helen, who Robert met while a postdoctoral fellow in NYC, have three children: Barney, Brendan, and Kathleen. All of Robert and Helen’s children hold either MD or PhD degrees.
Professor Grubbs began his independent research career by investigating mechanisms of a then obscure reaction called olefin metathesis, which had been reported separately by Giulio Natta (1963 Nobel prize), and researchers at DuPont and Phillips Petroleum. Robert’s studies, along with seminal investigations by Yves Chauvin (2005 Nobel Prize) and Thomas Katz, established the involvement of metal alkylidene and metallacyclobutane intermediates in the metathesis reactions. Robert was the first to isolate a metallacyclobutane, as a derivative of the Tebbe titanocene catalyst, and to use the derivative to prepare well-defined “living” polymers. Shortly thereafter, Richard Schrock (2005 Nobel Prize) and Robert reported a tungsten alkylidene catalyst that also initiated living polymerization. With the intention of identifying more reactive metal carbenes to promote polymerizations, the Grubbs’ group developed a ruthenium alkylidene catalyst that revolutionized organic synthesis and the preparation of polymers. These air and moisture stable catalysts were found to promote ring opening metathesis polymerization (ROMP) and ring closing metathesis (RCM) reactions with unprecedented functional group tolerance. The preparation of functionalized medium-size ring target molecules, which had long been among the biggest challenges in organic synthesis, became a matter of treating a diene tethered by the required number of intervening atoms with the Grubbs catalyst. Subsequent research into improving the reactivity of the ruthenium alkylidene catalysts by the Grubbs group led to the development of the Grubbs second-generation catalysts, which featured anN-heterocyclic carbene (NHC) ligand similar to that first prepared by Arduengo. Not only were the NHC-based catalysts more reactive, they were also more functional group tolerant and more environmentally stable than the earlier phosphine-based systems. Upon commercialization of the second-generation catalysts, manufacturers adopted the technology for applications ranging from the construction of more durable baseball bats, ballistic shields, and bathroom fixtures to the commercial preparation of pharmaceuticals. The catalysts also proved useful for creating functionalized, low polydispersity block copolymers with potential applications in medical diagnostics and materials science. In addition, bulk biorenewable organic compounds could be converted into fuels and commodity chemicals using Grubbs’ technology.
In recent years, Robert has continued to explore the mechanisms and development of superior metal alkylidene catalysts. He is also pioneering clever applications of olefin metathesis reactions. His recent investigations include the synthesis of insect pheromones as environmentally-friendly pest control agents, the construction of polymeric vapor sensing devices, and the preparations of customized lenses and treatments for various ocular disorders, biomedical adhesives and thin films, and drug delivery and molecular imaging agents. The Grubbs ruthenium alkylidenes and the metathesis reactions they promote are so integral to modern science that the catalysts and associated reaction mechanisms are now introduced in undergraduate chemistry curricula worldwide. Professor Grubbs’ landmark discoveries have transformed the strategy of organic synthesis, the methods employed for preparing molecules and materials, and the types of molecules and materials that can be prepared. One can only imagine what ingenious technology will come next from the Grubbs lab.
Professor Grubbs was an A. P. Sloan Fellow (1974-76), an Alexander von Humboldt Fellow (1975), and a Camille and Henry Dreyfus Teacher-Scholar (1975-78) early in his career. Robert has earned a multitude of awards since moving to Caltech. A partial list includes: an ACS Award in Organometallic Chemistry (1988), an A. C. Cope Scholar Award (1990), an ACS Polymer Chemistry Award (1995), Fluka Reagent of the Year Award (1998), a Benjamin Franklin Medal in Chemistry (2000), an ACS Herman F. Mark Polymer Chemistry Award (2000), an ACS H. C. Brown Award for Creative Research in Synthetic Methods (2001), an ACS Arthur C. Cope Award (2002), a Pauling Award Medal (2003), a Nobel Prize in Chemistry (2005), a Gold Medal of the American Institute of Chemists (2010), and an ACS Roger Adams Award in Organic Chemistry (2011). Robert was elected to the National Academy of Sciences in 1989 and named a Fellow of the American Academy of Arts and Sciences in 1994. To date, Robert has more than 500 publications and over 115 patents.