Sodium trifluoromethanesulfinate

Sodium trifluoromethanesulfinate
Names
IUPAC name
Sodium trifluoromethanesulfinate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.570
Properties
CF3NaO2S
Molar mass 156.05 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sodium trifluoromethanesulfinate (CF3SO2Na) is the sodium salt of trifluoromethanesulfinic acid. Together with t-butyl hydroperoxide, an oxidant, this compound was found to be a suitable reagent for introducing trifluoromethyl groups onto electron-rich aromatic compounds by Langlois; this reagent is also known as the Langlois reagent. This reaction operates via a free radical mechanism.[1]

This reagent is also able to trifluoromethylate electron-deficient aromatic compounds under biphasic conditions.[2] Zinc difluoromethanesulfinate, a related polymeric coordination complex, is able to introduce difluoromethyl groups (CHF2-) onto aromatic compounds under similar biphasic conditions as well.[3]

References

  1. ↑ Langlois, Bernard R.; Laurent, Eliane; Roidot, Nathalie (1991). "Trifluoromethylation of aromatic compounds with sodium trifluoromethanesulfinate under oxidative conditions". Tetrahedron Lett. 32 (51): 7525. doi:10.1016/0040-4039(91)80524-A.
  2. ↑ Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. (2011). "Innate C-H trifluoromethylation of heterocycles". Proc. Natl. Acad. Sci. 108 (35): 14411–5. doi:10.1073/pnas.1109059108. PMC 3167544. PMID 21844378.
  3. ↑ Fujiwara, Yuta; Dixon, Janice A.; Rodriguez, Rodrigo A.; Baxter, Ryan D.; Dixon, Darryl D.; Collins, Michael R.; Blackmond, Donna G.; Baran, Phil S. (2012). "A New Reagent for Direct Difluoromethylation". J. Am. Chem. Soc. 134 (3): 1494–7. doi:10.1021/ja211422g. PMC 3269891. PMID 22229949.

Further reading

  • Simon Hadlington (2011-08-15). "Trifluoromethylation made easy". RSC Chemistry World.
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