Sodium trifluoromethanesulfinate

Sodium trifluoromethanesulfinate

Structure of sodium trifluoromethylsulfinate
Names
Preferred IUPAC name Sodium trifluoromethanesulfinate
Identifiers
CAS Number	2926-29-6
3D model (JSmol)	Interactive image
ChemSpider	2059266
ECHA InfoCard	100.203.570
PubChem CID	23690734
CompTox Dashboard (EPA)	DTXSID50635644
InChI InChI=1S/CHF3O2S.Na/c2-1(3,4)7(5)6;/h(H,5,6);/q;+1/p-1 Key: KAVUKAXLXGRUCD-UHFFFAOYSA-M InChI=1/CHF3O2S.Na/c2-1(3,4)7(5)6;/h(H,5,6);/q;+1/p-1 Key: KAVUKAXLXGRUCD-REWHXWOFAL
SMILES [Na+].FC(F)(F)S([O-])=O
Properties
Chemical formula	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]

With the use of DMSO as an oxidant, it provides an environmentally friendly way for the synthesis of β-trifluoromethyl alcohols from alkenes. ^[4]

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. Bibcode:2011PNAS..10814411J. 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. Bibcode:2012JAChS.134.1494F. doi:10.1021/ja211422g. PMC   3269891 . PMID   22229949.
4. Shen, Wei-Guo; Wu, Qing-Yan; Gong, Xing-Yu; Liu, Feng; Ao, Guizhen (2019). "A facile method for hydroxytrifluoromethylation of alkenes with Langlois reagent and DMSO". Green Chemistry. 21 (11): 2983–2987. doi:10.1039/C9GC00886A. ISSN   1463-9262. S2CID   149671372.

Further reading

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