Princeton Docket #s 12-2718-1, 12-2719-1, 12-2720-1
Homogeneous catalysis with transition metals has transformed the art and science of chemical synthesis. The industrial synthesis of most commodity and fine chemicals, including pharmaceuticals, rely on one or more transition metal catalyzed steps. Traditionally these catalysts are based on precious metals of the second and third rows of the transition series and often suffer from high cost, toxicity, limited availability and pose environmental concerns. This new technology replaces these elements in homogeneous catalysis with more abundant and inexpensive base metals such as iron and cobalt.
It is anticipated that these new catalysts will be extremely useful in the pharmaceutical, agrochemical, food science, and flavors and fragrances industries.
The technology is a family of bis(imino)pyridine iron and or cobalt complexes that are versatile catalysts for a range of C-H, C-Si and C-C bond forming reactions. Key areas of application are olefin hydrogenation and hydrosilylation. The iron catalysts can also be used for for alkene hydrogenation and exhibit high turnover frequencies and broad functional group tolerance in that function. The technology also permits the creation of enantiopure products.
The catalysts compare favorably to those currently used in commercially practiced reactions. It has been demonstrated that the rate of the iron chemistry often surpasses the existing platinum processes. The specific cobalt compounds exhibit enantiomeric excess that rival known rhodium catalysts. Additionally, the iron compounds can also hydrogenate unactivated alkenes, a class of molecules not readily reduced by known precious metal catalysts.
Paul Chirik is the Edward S. Sanford Professor of Chemistry at Princeton University. Dr. Chirik received his Ph.D. from The California Institute of Technology in 2000. Prior to his appointment at Princeton, Professor Chirik was the Peter J.W. Debye Professor of Chemistry and Chemical Biology at Cornell University. He is the recipient of several notable awards including: the Arthur C. Cope Scholar Award, American Chemical Society, the Bessel Fellowship of the Alexander von Humboldt Foundation, the Camille Dreyfus-Teacher Scholar, the Stephen and Margery Russell Distinguished Teaching Award, the David and Lucile Packard Fellow in Science and Engineering, and the NSF CAREER Award. He is also a member of the Defense Science Study Group focused on technological solutions to problems in national security.
Research in the Chirik group is at the intersection of the traditional disciplines of organic and inorganic chemistry. The discovery of sustainable methods in chemical synthesis is a unifying theme. One area of long-standing interest is the discovery of new reactions for the functionalization of atmospheric nitrogen. A second interest is base metal catalysis and the elucidation of the electronic structure of redox-active metal-ligand complexes with emphasis on the integration of spectroscopy and theory. With these goals in mind, they study transition metal complexes from across the periodic table and use state-of-the-art multinuclear NMR experiments, X-ray diffraction techniques, isotopic labeling, Mössbauer and EPR spectroscopy as well as modern DFT methods to establish the electronic and molecular structures of the compounds and pre-catalysts they prepare.
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