DesignandApplicationofHydrophilicLigandsforAqueous-.docxVIP

Design and Application of Hydrophilic Ligands for Aqueous-Phase Metal-Catalyzed Organic Reactions Weijia GAN 06 Jun 2011 Questions? How to improve the mass transport issue in aqueous-biphasic system? How the hydrophilic functionalities could influence the ligand properties (water solubility, steric and electronic effects)? Outline Introduction Why and how to use water as the solvent for organic reactions Strategies to perform organic reaction in water using hydrophilic ligands Examples of aqueous-phase hydroformylation Examples of the application of the hydrophilic ligands on some typical organic reactions Hydrogenation; metathesis; cross-coupling; oxidation; etc. Conclusions and perspectives Solvent of life - water Water covers more than 70.9% of the earth’s surface and makes up about 60% of the mass of the human body. Water plays an important role in the world economy as it functions as solvent for a wide variety of chemical substances and facilitates industrial cooling and transportation. Organic solvents vs. water Organic solvents Dissolve a wide range of organic compounds A variety of options and properties Volatile and easily removed Toxic, inflammable, nonrenewable, low heat capacities, etc. Water Nontoxic Nonflammable High heat capacity Relatively inexpensive Green solvent Poor solvent for most organic molecules Highly reactive with many reagents. Homogeneous metal catalyzed reactions Homogeneous catalysts offer unparalleled degrees of selectivity and tunability from Similar solubility characteristics of the catalyst and product – how to recover the metal from the product? Pioneering industrial processes: Wacker oxidation; olefin hydroformylation Modern processes: asymmetric hydrogenation; Pd-catalyzed cross-coupling; olefin metathesis, etc. How to recover the catalyst? Catalyst immobilization To heterogenize the homogeneous catalyst by attaching it to a solid support, allowing the catalyst to be recovered in the same way as traditional heterogeneous cata