New Technologies Based on Organocopper Catalysis

University Of California-Santa Barbara, Santa Barbara CA

Investigators

Abstract

This project will explore several synthetic methods that rely on copper as the metal that effects catalysis. A number of the transformations are on copper hydride chemistry, which includes new uses of nonracemically ligated CuH for syntheses. The potential to realize unprecedented ligand-accelerated catalysis with CuH in pure water at room temperature will be pursued, along with the potential to deliver water-sensitive carbon-based residues via conjugate addition chemistry, with both approaches based on micellar catalysis in water. Heterogeneous processes that take advantage of both readily accessed valence states of copper [Cu(I) and Cu(II)] impregnated into the pores of inexpensive charcoal matrices will also be developed. A high substrate-to-ligand ratio and tandem processes that can be carried out in a single reaction vessel will be studied. With this award, the Chemical Synthesis Program is supporting the research of Professor Bruce H. Lipshutz of the Department of Chemistry at the University of California, Santa Barbara. Professor Lipshutz's research efforts revolve around the development of organocopper-based asymmetric catalysis leading to new methods for the formation of C-C and C-H bonds. Such chemistry will contribute to environmentally benign methods for chemical synthesis as most of these new technologies will be developed in the absence of organic solvents, where water serves as the macroscopic medium. Successful applications of the methodology will have an impact on synthesis in the pharmaceutical, fine chemical, and agricultural industries.