Chemistry:Sodium trifluoromethanesulfinate
| |
| Names | |
|---|---|
| Preferred IUPAC name
Sodium trifluoromethanesulfinate | |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
| |
| |
| 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]
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
- ↑ 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.
- ↑ 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. PMID 21844378. Bibcode: 2011PNAS..10814411J.
- ↑ 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. PMID 22229949.
- ↑ 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" (in en). Green Chemistry 21 (11): 2983–2987. doi:10.1039/C9GC00886A. ISSN 1463-9262.
Further reading
- Simon Hadlington (2011-08-15). "Trifluoromethylation made easy". RSC Chemistry World. http://www.rsc.org/chemistryworld/News/2011/August/15081102.asp.
 |  |
