This CAREER Award in the Inorganic, Bioinorganic and Organometallic Chemistry Program supports the research and education plans of David S. Glueck of Dartmouth College. The goal of the proposed research is to understand the formation of phosphorous-carbon (P-C) bonds to develop metal-catalyzed syntheses of chiral phosphines and to design phosphine ligands resistant to P-C bond cleavage. Mechanistic studies of reductive elimination and oxidative addition reactions with organophosphorous species will guide chiral catalyst development and test the hypothesis that arylphosphines with electron-donating substitutents will resist degradation. A new course will be developed to improve the scientific literacy of liberal arts students by taking an interdisciplinary look at a few top industrial chemicals. The industrial chemistry, economics, and environmental impacts of these chemicals will be explored.