What are Fluorous Molecules ?
Fluorous Technology Primer - Part I
Fluorous molecules are designed to mimic organic molecules in terms of reactivity yet to still be readily separable from other organic molecules. In the technique of fluorous mixture synthesis, fluorous molecules are also separated from each other. Fluorous molecules typically have two domains. The organic domain resembles a standard organic parent molecule and dictates the reactivity of the molecule. The fluorous domain is a highly fluorinated group that controls the separation features of the molecule. Fluorous domains are often perfluoroalkyl groups.
Shown on the right are two simple examples of fluorous molecules designed after common organic parents. Fluorous tin hydrides have similar reactivity to the classical reagent tributyltin hydride. But unlike tributyltin compounds, the fluorous tin compounds are readily separable from organic compounds by simple fluorous separation techniques like liquid-liquid extraction or solid-liquid extraction. The fluorous domain of the tin hydride is permanently attached because there is never any need to separate it from the organic domain. The tin compounds are simply recovered at the end of the reaction and recycled. Although only one tin hydride is shown below, a whole family is available from FTI whose members differ from each other by the length and number of the fluorinated chains and the length of the spacer. This allows the separation properties and (sometimes) the reactivity properties to be tuned for particular needs.
The fluorous Boc group is a typical example of a fluorous protecting group that is designed to be attached and removed by analogy with the standard Boc group. Such fluorous protecting groups are also called fluorous tags, and they allow rapid separation of all tagged molecules from non-tagged molecules by fluorous solid phase extractions. A growing assortment of fluorous tags is now available.
Our Technology Primer - Table of Contents
1. Introduction: What are Fluorous Molecules ?2. Fluorous Separation Methods
3. Fluorous Biphasic Catalysis
4. Fluorous Triphasic Reactions
5. Fluorous Reagents, Reactants and Catalysts
6. Fluorous Substrates and Products (Fluorous Synthesis)
7. Fluorous Mixture Synthesis
8. Summary