Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Fe2O3-Promoted Intermolecular Chlorotrifluoromethylthiolation of Alkenes

Fe2O3-Promoted Intermolecular Chlorotrifluoromethylthiolation of Alkenes
Zhong-Xing Jiang, Hongmei Qin, Na Wang, Yimin Jia, Zhigang Yang
A simple, convenient method for intermolecular chlorotrifluoromethylthiolation of alkenes by using a low-cost and more abundant iron catalyst has been developed. This protocol provides a straightforward way to synthesize a variety of useful SCF3-containing chlorides from a wide range of alkenes, including electron-deficient, aromatic, and unactivated alkenes. Mechanistic studies indicate that this is a free radical transformation, and the stronger electrophilic trifluoromethylthiolating reagent CF3SCl was generated in situ under the employed conditions. The synthetic applications of this approach were also explored by a variety of synthetically useful transformations.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b03261

DOI: 10.1021/acs.joc.7b03261

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