Fluorous chemistry

Fluorous chemistry is chemistry that uses perfluorinated compounds, commonly the fluorosurfactant perfluorooctanoic acid (PFOA). Due to the extreme electronegativity of fluorine, perfluorinated compounds have unique physical properties which are useful in organic synthesis and separation methods such as solid phase extraction.[1] In practice, a perfluorinated alkane is often incorporated into an otherwise conventional organic reagent as an affinity tag to facilitate recovery of a catalyst, reaction product, or reaction byproduct. The rationale for using fluorous tags in synthesis or separation is the notion of the fluorous phase, a partitioning modality distinct from polar/non-polar or hydrophilic/hydrophobic.[2] Although many fluorochemicals are known to have toxic effects, the high affinity of fluorous tags for fluorous phases or fluorous-derivatized solid phases allows for near complete recovery of the tagged reagent (i.e., near complete reduction in a chemical waste stream), making the use of fluorous chemistry techniques a popular topic in green chemistry.[3]

References

  1. ^ Zhang, W.; Curran, D. P. (2006). "Synthetic Applications of Fluorous Solid-Phase Extraction (F-SPE)". Tetrahedron 62 (51): 11837–11865. doi:10.1016/j.tet.2006.08.051. PMC 2396515. PMID 18509513. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2396515. 
  2. ^ Yu, M. S.; Curran, D. P.; Nagashima, T. (2005). "Increasing Fluorous Partition Coefficients by Solvent Tuning". Org. Lett. 7 (17): 3677–3680. doi:10.1021/ol051170p. PMID 16092848. 
  3. ^ E.G. Hopea, A.P. Abbotta, D.L. Daviesa, G.A. Solana and A.M. Stuarta “Green Organometallic Chemistry” in Comprehensive Organometallic Chemistry III, 2007, Volume 12, Pages 837-864. doi:10.1016/B0-08-045047-4/00182-5