Scientists in Japan have used a by-product of Teflon manufacture to generate carbonyl compounds with trifluoromethyl groups. Organic molecules bearing a trifluoromethyl group have received much attention because of their unique physical and chemical properties, which are important in the fields of medicinal, agrichemical and materials sciences, say the researchers. Efficient ways of introducing CF3 groups into target molecules are being sought. The nucleophilic trifluoromethylation of carbonyl compounds using a Ruppert–Prakash reagent – (trifluoromethyl)trimethylsilane – is a well-explored strategy. But, (trifluoromethyl)trimethylsilane is expensive to prepare and is prepared from ozone-depleting bromotrifluoromethane. Fluoroform – a by-product of Teflon manufacture – has emerged as a potential environmentally benign alternative to (trifluoromethyl)trimethylsilane. It is also non-toxic, cheap and available in large quantities.
A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform
Hiroyuki Kawai, Zhe Yuan, Etsuko Tokunaga and Norio Shibata
Org. Biomol. Chem., 2013,
DOI: 10.1039/C3OB27368G
