Base Metal Catalysis for Organic Synthesis: The Interplay of Applications and Electronic Structure

February 13, 2015

Paul Chirik

Transition metal catalysis has revolutionized organic synthesis by enabling new transformations with unprecedented selectivity. Our laboratory has been actively engaged in developing catalysts based on earth abundant elements rather than more traditionally deployed precious metals. The inspirations for this chemistry extend beyond catalyst cost; ultimately we aim to discover new reactivity that exploits the unique electronic structures of first row transition metals. My lecture will focus on two complementary approaches to this challenge. The first explores redox-active ligands, those that engage in reversible radical chemistry with the metal center, while the second employs a more traditional strong field ligand approach to engender more electron rich metal complexes. These two extremes define a continuum of reactivity ranging from new iron catalysts for commercial silicone production (Science 2012, 335, 567) to the asymmetric hydrogenation of alkenes (Science 2013, 342, 1054) and C-H functionalization (J. Am. Chem. Soc. 2014, 136, 4133), important transformations with pharmaceutical relevance. Through continued ligand evolution and understanding of electronic structure, we have discovered base metal catalysts that promote chemistry unknown with established precious metal variants. The mechanisms of the various catalytic transformations and the importance of electronic structure controlled through ligand manipulation will be a highlighted throughout.

Speaker Bio    

Paul Chirik was born in 1973 outside of Philadelphia, PA. In 1995 he earned his Bachelor of Science in Chemistry from Virginia Tech. During that time, he conducted undergraduate research with Professor Joseph S. Merola studying aqueous iridium chemistry. Chirik earned his Ph. D. with Professor John Bercaw at Caltech in 2000 and was awarded the Hebert Newby McCoy award for his dissertation on metallocene catalyzed olefin polymerization. After a brief postdoctoral appointment with Professor Christopher Cummins at MIT, Chirik began his independent career at Cornell University in 2001. In 2006, he was promoted to Associate Professor and in 2009 was named the Peter J. W. Debye Professor of Chemistry. In 2011, Chirik and his research group moved to Princeton University where was named the Edward S. Sanford Professor of Chemistry. His teaching and research have been recognized with an Arthur C. Cope Scholar Award, the Blavatnik Award for Young Scientists, a Packard Fellowship in science and engineering, a Camille Dreyfus Teacher Scholar Award and an NSF CAREER Award. He is currently the Editor-in-Chief of Organometallics.