Issue Date: August 4, 2014
Sweet Fluorinating Agent From Saccharin
The trifluoromethylthio group, SCF3, is one of the most lipophilic functional groups known and as such has attracted the attention of chemists who develop pharmaceuticals and pesticides. Chunfa Xu, Bingqing Ma, and Qilong Shen of Shanghai Institute of Organic Chemistry have now developed a trifluoromethylthiolating reagent that should make life easier for those researchers (Angew. Chem. Int. Ed. 2014, DOI: 10.1002/anie.201403983). Chemists currently use CF3SCl as a direct trifluoromethylthiolating reagent, but it is a toxic gas. Other strategies such as adding sulfur and CF3 to a compound tend to require multiple steps and have limited synthetic applications. An alternative that is meeting with some success is creating N-substituted SCF3 reagents (Chem. Eur. J. 2014, DOI: 10.1002/chem.201403409). Building on the latter approach, the Shanghai team used the inexpensive artificial sweetener saccharin and AgSCF3 to create the new reagent. It works well for adding SCF3 to a variety of organic compounds under mild conditions to prepare OSCF3, NHSCF3, SSCF3, and SCF3 derivatives. Shen and coworkers have applied for Chinese patents on the saccharin reagent and are working with a Chinese company to produce it for industrial and research use.
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