FluoroFlash® SPE Cartridges for Fluorous Separations

ChemFiles Volume 4 Article 9

Fluorous Solid Phase Extraction (F-SPE) is used for quick separations of reaction mixtures involving fluorous reagents, protecting groups, tags, and scavengers.[1-6] FluoroFlash® SPE Cartridges are pre-packed in a variety of formats with a proprietary silica gel bonded with perfluoroalkyl chains. FluoroFlash® Silica Gel separates compounds based primarily on fluorous content. Fluorous molecules are selectively retained while non- fluorous compounds are eluted regardless of polarity. This results in a simple two-step separation of fluorous compounds from non-fluorous compounds. Following completion of a reaction using a fluorous-tagged molecule, the reaction mixture is loaded onto a F-SPE cartridge. Using a fluorophobic wash, typically 80:20 MeOH:H2O, the non-fluorous organic compounds are washed off the cartridge. The fluorous compounds are then washed off the cartridge using a fluorophilic second wash such as MeOH, acetone or THF.[6] The loading capacity for fluorous SPE is typically between 5 and 15% by weight of fluorous silica gel. The cartridge can be regenerated by washing thoroughly with acetone or THF and reused up to 10 times. Multiple fraction collection and analysis are not required as there is one organic wash and one fluorous wash. Due to the large separation, loading levels can be very high. Since the separation process is highly reproducible and functional group independent, it can be easily automated.

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Materials

     

References

  1. Curran, D. P. Synlett 2001, 1488;
  2. Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855; 
  3. Luo, Z.; Williams, J.; Read, R. W.; Curran, D. P. J. Org. Chem. 2001, 4261; 
  4. Zhang, W. Org. Lett. 2003, 5, 2555; 
  5. Zhang, W.; Curran, D. P.; Chen, C. Tetrahedron 2002, 58, 3871. Lindsley, C. W.; Zhao, Z.; Leister, W. Tetrahedron Lett. 2002, 43, 4225; 
  6. Zhang, W.; Luo, Z.; Christine, C.; Curran D. P. J. Am. Chem. Soc. 2002, 124.

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