• DOI:10.1126/science.1227859
• Corpus ID: 206544170

Taming of Fluoroform: Direct Nucleophilic Trifluoromethylation of Si, B, S, and C Centers

@article{Prakash2012TamingOF,
  title={Taming of Fluoroform: Direct Nucleophilic Trifluoromethylation of Si, B, S, and C Centers},
  author={G. K. Surya Prakash and Parag V. Jog and Patrice T D Batamack and George A. Olah},
  journal={Science},
  year={2012},
  volume={338},
  pages={1324 - 1327}
}

• G. Prakash, Parag V. Jog, +1 author G. Olah
• Published 7 December 2012
• Chemistry
• Science

CF3 from Fluoroform Fluoroform (CF3H) is a by-product from the manufacture of fluorocarbon-based materials used, for example, in nonstick coatings and refrigerants. Fluoroform's potency as a greenhouse gas is a growing concern as supplies continue to accumulate. In this context, Prakash et al. (p. 1324; see the Perspective by Haufe) show that fluoroform can be used to transfer CF3 to silicon, sulfur, and carbon centers in the development of CF3-bearing pharmaceutical and agrochemical structures. Proper choice of base and solvent renders fluoroform a useful reagent to introduce trifluoromethyl groups into a range of compounds. Fluoroform (CF3H), a large-volume by-product of the manufacture of Teflon, refrigerants, polyvinylidene fluoride (PVDF), fire-extinguishing agents, and foams, is a potent and stable greenhouse gas that has found little practical use despite the growing importance of trifluoromethyl (CF3) functionality in more structurally elaborate pharmaceuticals, agrochemicals, and materials. Direct nucleophilic trifluoromethylation using CF3H has been a challenge. Here, we report on a direct trifluoromethylation protocol using close to stoichiometric amounts of CF3H in common organic solvents such as tetrahydrofuran (THF), diethyl ether, and toluene. The methodology is widely applicable to a variety of silicon, boron, and sulfur-based electrophiles, as well as carbon-based electrophiles.