Rf-tagged Nucleophilic Scavengers

Chemfiles Volume 4 Article 9

F-Thioles

Thiols are good nucleophiles that have been used as covalent scavengers to rid product mixtures of excess halides and other electrophiles. F-Thiol is the solution-phase equivalent of polymer bound thiol scavengers. It has the advantage of reacting faster than its polymer counterpart.[1] F-Thiol-quenched derivatives can be easily separated from the organic product by performing a quick solid-phase extraction over FluoroFlash® silica gel.[2,3]

F-Thiols can also serve as fluorous tags in parallel synthesis.[4] Tagging is achieved by nucleophilic substitution of a halide by the thiol. Detagging is achieved by oxidation of the sulfide to a sulfone followed by nucleophilic substitution by another nucleophile.

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Materials

     

References

  1. Zhang, W.; Curran, D. P.; Chen, H.-T. Tetrahedron 2002, 3871
  2. Curran, D. P. Synlett 2001, 1488
  3. Lindsley, C. W.; Zhao, Z.; Leister, W. H.; Strauss, K. A. Tetrahedron Lett. 2002, 43, 6319
  4. Zhang, W. Org. Lett. 2003, 5(7), 1011.

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