Sodium trifluoromethanesulfinate explained
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
- 10.1016/0040-4039(91)80524-A . Tetrahedron Lett. . Trifluoromethylation of aromatic compounds with sodium trifluoromethanesulfinate under oxidative conditions . 1991 . Langlois . Bernard R. . Laurent . Eliane . Roidot . Nathalie . 32 . 51 . 7525.
- 10.1073/pnas.1109059108 . Proc. Natl. Acad. Sci. . Innate C-H trifluoromethylation of heterocycles . 2011 . Ji . Y. . Brueckl . T. . Baxter . R. D. . Fujiwara . Y. . Seiple . I. B. . Su . S. . Blackmond . D. G. . Baran . P. S. . 108 . 35 . 14411–5 . 21844378 . 3167544 . 2011PNAS..10814411J . Phil S. Baran. free .
- 10.1021/ja211422g . J. Am. Chem. Soc. . A New Reagent for Direct Difluoromethylation . 2012 . Fujiwara . Yuta . Dixon . Janice A. . Rodriguez . Rodrigo A. . Baxter . Ryan D. . Dixon . Darryl D. . Collins . Michael R. . Blackmond . Donna G. . Baran . Phil S. . 134 . 3 . 1494–7 . 22229949 . 3269891.
- 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. en. 10.1039/C9GC00886A. 149671372 . 1463-9262.
Further reading
