Wei Zhang, University of Massachusetts - Boston, Boston, MA
This presentation highlights our four areas of research on the development of fluorous techniques for making organic synthesis a greener and more efficient process. 1) Fluorous molecules are lipo- and hydrophobic. This property has been utilized in the separation of fluorous molecules from non-fluorous organic molecules. Since recovered fluorous reagents and catalysts have minimal non-fluorous byproduct contamination, they generally can be reused for next round of reaction without significant effort on purification. 2) Microwave irradiation is an efficient and controllable energy source for organic synthesis. Many microwave reactions can be conducted under the solvent-free conditions. The combination of fluorous tagging strategy and microwave reactions can significantly reduce the reaction time and simplify the product purification process. This presentation will give several examples to demonstrate the good thermal stability and reactivity of fluorous molecules under microwave conditions. 3) Multicomponent reactions (MCRs) have a strong green chemistry aspect since the formation of a complex molecule can be accomplished in a one-pot reaction process that requires less energy and generates less waste. Fluorous tag-attached component can improve the purification efficiency of MCRs. They have been applied to Ugi/deBoc/cyclization reactions and 1,3-dipolar cycloaddtion/Suzuki coupling reactions. 4) Catalysis is an important area of green chemistry research. The recent development of organocatalysis has provided a new approach to replace the use of toxic heavy metal catalysts. However, high catalyst loading and lack of general methods for catalyst recovery are two major issues associate with the organocatalysis. We have completed the synthesis of a fluorous version of imidazolidinone catalyst and compared it with the normal imidazolidinone in asymmetric Diels-Alder reactions. The fluorous catalyst has comparable reactivity and enantioselectivity, but the recovered fluorous catalyst has higher yield and purity. Extension of our preliminary results for making more fluorous recoverable organocatalysts will be discussed in the presentation.