Forming Carbon-Carbon Bonds in Water and Other Alternative MediaEPA Grant Number: R828129
Title: Forming Carbon-Carbon Bonds in Water and Other Alternative Media
Investigators: Li, Chao-Jun
Institution: Tulane University of Louisiana
EPA Project Officer: Hahn, Intaek
Project Period: June 1, 2000 through May 31, 2003 (Extended to September 24, 2004)
Project Amount: $310,000
RFA: Technology for a Sustainable Environment (1999) RFA Text | Recipients Lists
Research Category: Sustainability , Pollution Prevention/Sustainable Development
The long term objective of the proposed research is to develop various environmentally friendly chemical syntheses using water, liquid CO2, and ionic liquid as non-polluting solvents.
Metal-mediated carbon-carbon bond formation is one of the most important fundamental reactions in organic chemistry and is widely used in various chemical and pharmaceutical processes. Traditionally, they are carried out in anhydrous organic solvents and are air-sensitive and are potentially explosive. The present study investigates the scope, mechanism and synthetic application of metal-mediated reactions through the use of water solvents. The synthesis of various biologically important compounds and fine chemicals are to be investigated through the aqueous method. The method saves synthetic steps by avoiding many protection and deprotection processes and contributes to overall synthetic efficiency and a reduction in organic emission. Additional research is planned to transform the reaction into a catalytic process. Additionally, the use of liquid CO2 and ionic liquid as non-polluting solvents for carbon-carbon bond formations will also be investigated.
The present study would establish the foundation of developing the aqueous metal-mediated reaction into a general process that does not use anhydrous organic solvents, avoids the use of protection-deprotections, is applicable to large scale industry operation, and has a reduced impact on environment due to the use of catalytic amount of metal and/or in-process recycling. The present project also provides basic understandings of using liquid CO2 and ionic liquids for carbon-carbon bond formations.
Chemical technologies developed herein will significantly enhance the efficiency of chemical synthesis and reduce the amount of organic waste in reactions and product isolations by saving synthetic steps due to the elimination of many functional group protection/deprotection steps. All these alternative solvents can be readily purified and recycled for further reactions which further prevent the discharge of chemical wastes.