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Fluorous Technologies, Inc. (FTI) can meet all of your product needs for any scavenging application or use. Sold under the FluoroFlash® trade name, FTI provides the scavengers, reagents, and sorbents to meet your chemistry needs. Go directly to our product catalog pages by clicking on the product categories above or, read on and learn more about this exciting new application of fluorous chemistry. To download a PDF version of our catalog, please click here.
Fluorous covalent scavengers bear familiar nuleophilic, electrophilic, and other scavenging functional groups, modified to include a perfluoroalkyl chain. These chains, or fluorous tags, allow the rapid separation of the scavenged products from target products by Fluorous Solid Phase Extraction (F-SPE). The product chart shows examples of FluoroFlash® covalent scavengers along with some of the functional groups they can be used to target.
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Scavenging is an exciting new application of fluorous technology. It unites the attractive features of solution phase chemistry with the convenient workup of solid phase extraction. Fluorous scavengers have distinct advantages over more conventional polymer and ionic scavengers. When used in combination with FluoroFlash® products, including other reagents and sorbents, fluorous scavengers provide the following benefits:
In a side-by-side comparison, researchers at FTI have shown that FluoroFlash® scavengers outperform solid phase scavengers (based on the reaction shown.) [1] Furthermore, fluorous scavenging reactions are not limited to electrophilic and nucleophilic chemistries, making a full range of scavenging chemistries accessible.
ln a typical process, an excess of one reagent starting materials is used to rapidly drive a solution phase reaction to completion (Figure1). The final mixture is composed of the desired product and one or more byproducts (either excess reagents and/or spent reagents). The soluble fluorous scavenger is then introduced and scavenges the byproducts to form fluorous-tagged compounds. Rapid fluorous solid phase extraction (F-SPE) of the reaction mixture retains the scavenged byproducts and any unreacted scavenger while allowing the target product to quickly pass through.
Fluorous compounds used in these reactions are referred to as "light fluorous" scavengers because they are usually <40% fluorine content by molecular weight. Light fluorous scavengers used in conjunction with this method can be applied in many discovery applications.
Fluorous scavenging reagents are also convenient caps of unreacted functional groups in solid phase synthesis. After cleaving products from the solid phase, the truncated fluorous products are readily separated from the target products by F-SPE or chromatography. By taking advantage of the unique properties of fluorous compounds, peptide oligomers of 7-22 amino acids produced using traditional solid phase methods are quickly and reliably purified. [5] An analogous strategy incorporates the use of fluorous scavenging technology in the synthesis of oligosaccharides. In this case, however, the fluorous portion is a "captag" which is used to render the undesired material fluorous, while the desired oligomeric species is non-fluorous. [4]
Post-reaction fluorous tagging is not limited to removal of undesired products. When a number of different side products are present, FluoroFlash® scavengers can selectively capture the desired product from either a solution or a solid phase synthesis using the same basic process described above.
Microwave assisted fluorous synthesis techniques provide a useful method of speeding fluorous reactions.
Based on the reaction conditions and the nature of the fluorous scavenger employed, there are three major variations to the standard light fluorous scavenging paradigm depicted in Figure 2. [6]
Using "heavy fluorous" scavengers (those containing >60% fluorine by molecular weight) and liquid/liquid separation and extraction methods three processes are described for the scavenging of particular classes of compounds. [3][6]
The use of fluorous chemistries in solution phase synthesis processes has emerged as a unique and effective paradigm. In the following examples fluorous scavengers are employed as quenching agents in the synthesis of various products, including parallel library synthesis applications. [1][7][8]
In the medicinal chemistry arena, the use of solution phase parallel synthesis processes in the creation of analog arrays based on high throughput screening hits is a crucial step in the drug discovery process. Here fluorous scavengers are used to overcome many of the limitations of resin-bound reagents. [2][3]
Linclau, Bruno; Sing, Ashvani K.; Curran, Dennis P. Organic-Fluorous Phase Switches: A Fluorous Amine Scavenger for Purification in Solution Phase Parallel Synthesis J. Org. Chem. 1999, 64, 2835-2842 [PDF Article]
Curran, Dennis P.; Hadida, Sabine; Kim, Sun-Young; Luo, Zhiyong Flurous Tin Hydrides: A New Family of Reagents for Use and Reuse in Radical Reactions J. Am. Chem. Soc. 1999 , 121, 6607-6615 [PDF Article]