ORGN 898 |
| Fluorous synthesis is a “beadless” high-throughput synthetic technology which employs perfluoroalkyl chains instead of resins as “phase tags” to facilitate the separation process. The separation is achieved by strong and selective interactions between fluorous molecules with fluorous solvents or sorbents. Fluorous technologies integrate homogeneous solution-phase reactions and phase-tag separations and have advantages of fast reaction kinetics; easy purification by fluorous methods as well as none-fluorous methods; using slightly excess of fluorous reagents to complete reactions; and recoverable of fluorous species. This presentation describes recent advance of following fluorous silica gel-based separation techniques. 1) Plate-to-plate solid-phase extraction (SPE). Large particle size fluorous silica gel and a water-free elution solvent system have been developed for gravity-driven 24-, 48- and 96-well plates SPE of compound libraries generated from parallel reactions. 2) Automated SPE. Fluorous-SPE has been successfully implemented to RapidTrace SPE station and demonstrated in fluorous amide coupling and scavenging reactions. 3) Flash chromatography. Using the Biotage FlashMaster system, we have achieved variable scale separations of fluorous intermediates in library synthesis. 4) Fluorous HPLC can be used for analytical and prep-scale separation of fluorous samples. Applications of F-HPLC in fluorous mixture synthesis (FMS) and MS-directed parallel HPLC for high-throughput purifications are also described.
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Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 132, Oral
Division of Organic Chemistry |