Issue Date: February 2, 2009
ACS Award For Creative Invention
Sponsored by Corporation Associates
The olefin metathesis catalysts invented by Robert H. Grubbs have had a far-reaching impact on the field of synthetic organic chemistry, easing the production of pharmaceuticals, materials, and fine chemicals.
"His investigations have had unparalleled impact on the development of well-defined complexes that function as catalysts for organic synthesis," says David W. C. MacMillan, a professor of chemistry at Princeton University and the director of the school's Merck Center for Catalysis.
Based on ruthenium alkylidenes, Grubbs's olefin metathesis catalyst systems exhibit unprecedented tolerance toward a vast array of functional groups. The catalysts are now employed on a global scale for ring-closing metathesis, ring-opening metathesis, and cross-olefin metathesis. The swaths of molecules they are used to produce include hepatitis C drugs, pheromones for pesticide applications, and robust polymers for agricultural and deep-sea applications.
Grubbs, 66, was born in a rural town in Kentucky. He attended the University of Florida as an undergraduate, earning a B.S. in chemistry in 1963. Two years later, he earned his master's degree also from the University of Florida, under the guidance of Merle A. Battiste, a research director who steered Grubbs away from agricultural chemistry and toward organic chemistry. An added incentive, Grubbs explained in 2005, was that he "found that organic chemicals smelled much better than steer feces and that there was great joy in making new molecules."
In 1968, Grubbs earned a Ph.D. in chemistry from Columbia University. Over the next year, he completed a National Institutes of Health postdoctoral fellowship at Stanford University. He began his independent academic career in what he recalls was a very supportive environment at Michigan State University before accepting an offer to join the chemistry department at California Institute of Technology in 1978. He has remained at Caltech ever since, currently holding rank as the Victor & Elizabeth Atkins Professor of Chemistry.
In 1980, Grubbs isolated and characterized the first metallacyclobutane complex capable of catalyzing the olefin metathesis reaction. An important outcome of this work was the discovery of a new class of polymerization catalysts for producing living polymerizations with metallacyclic end groups.
Grubbs, along with coworker Gregory C. Fu, revealed in 1992 that ring-closing metathesis is an efficient, selective, and general method of intramolecular ring closure. That same year, Grubbs introduced his first ruthenium catalyst for olefin metathesis. Four years later, he introduced a ruthenium catalyst with better activity and substrate tolerance. That catalyst, (PCy3)2Cl2RuCHC6H5 (Cy = cyclohexyl), is now widely known as the Grubbs catalyst. In 1999, Grubbs introduced the so-called second-generation Grubbs catalyst, which boasts even better activity and an N-heterocyclic ligand in place of one of the Grubbs catalyst's tricyclohexylphosphines.
"Nothing advances chemistry, and thereby the many practical fields dependent on it, more than the discovery of useful and completely unprecedented reactivity," a colleague says. "I sense that, thanks to the discoveries in the Grubbs group, we are now living through one of those rare moments in chemical history."
Over the past three decades, the accolades have piled up for this husband and father of three. They include the 2005 Nobel Prize in Chemistry, the 2002 Arthur C. Cope Award, and the 2003 ACS Award for Creative Research in Homogenous or Heterogeneous Catalysis. Such recognition has landed Grubbs appointments to more than 40 committees and advisory boards since 1981, many of which he currently still holds.
With literally hundreds of research groups and companies around the world using Grubbs's catalysts and students and researchers alike clamoring to work in his lab, Grubbs has more than earned this latest honor.
Grubbs will present the award address before the Division of Organic Chemistry.
- Chemical & Engineering News
- ISSN 0009-2347
- Copyright © American Chemical Society