Rf-tagged Silanes

ChemFiles Volume 4 Article 9

F-Silanes are fluorous equivalents to a TIPS group and exhibit properties similar to most silicon protecting groups. Silanes have been used as fluorous tags in both parallel and fluorous mixture synthesis (FMS).1,2 Tagging of an alcohol is accomplished by in situ activation of the F-Silane to either the bromide or the triflate followed by addition of the alcohol. The tagged molecule can be manipulated over a number of chemical steps before detagging with fluoride. The tagged intermediates are quickly and easily separated after each step from organic reagents, reactants, or products by fluorous solid-phase extraction (F-SPE) over FluoroFlash® Silica Gel.3

 

References

  1. Luo, Z. Y.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766;
  2. Zhang, W.; Luo, Z.; Chen, C. H.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443;
  3. Curran, D. P. Synlett 2001, 1488.

 

 

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