Metal Reagents for Activation and Functionalization of Carbon-Fluorine Bonds

Abstract

The distinctive physical properties of fluorocarbons derived from the great strength of the C-F bond often result in chemical compounds with unique properties and technologically useful applications. However, this same factor conspires to make fluorocarbons unreactive under most conditions. In the past decade it has become clear that metal reagents provide a unique tool for activation and functionalization of the C-F bond under mild conditions. Fundamental approaches toward the activation of C-F bonds are discussed with an emphasis on transition metal reagents. Intramolecular systems provided the intellectual foundation for the development of intermolecular C-F bond activation chemistry. Mechanistic studies of model systems give an indication of the scope of this process. Exciting recent advances in the catalytic chemistry of the C-F bond in fluorinated aromatic and aliphatic systems will be described. Selective C-F bond activation is a key requirement for the application of these reagents in organic synthesis. Theoretical and gas phase studies which provide insight into the mechanisms of these reactions will be discussed.