Volume 91 Issue 45 | p. 27 | Concentrates
Issue Date: November 11, 2013

Palladium-Activated Fluoroform

Easy reaction of CHF3 with versatile palladium complex is expected to aid sustainable use of fluorinated chemicals
Department: Science & Technology
News Channels: Organic SCENE, Environmental SCENE, Materials SCENE, JACS In C&EN
Keywords: fluoroform, fluorination, fluorine chemistry, greenhouse gas, trifluoromethylation

Trifluoromethane (CHF3), also known as fluoroform or HFC-23, is a large-volume side product of fluoropolymer production. Although the compound is ozone-friendly, it’s a potent greenhouse gas that manufacturers must pay to destroy. Chemical firms would like to repurpose CHF3 as an inexpensive feedstock for fluorinated pharmaceuticals and agrochemicals. But chemists need efficient methods to activate CHF3’s strong and poorly reactive C–H bond. Researchers recently discovered zinc-, copper-, and iridium-mediated CHF3 reactions. Shin Takemoto (visiting from Japan’s Osaka Prefecture University) and Vladimir V. Grushin of the Institute of Chemical Research of Catalonia, in Spain, continuing Grushin’s work on copper, now report the first example of CHF3 activation with palladium(II) (J. Am. Chem. Soc. 2013, DOI: 10.1021/ja409533s). The phosphine-catalyzed reaction leads to aryl PdCF3 complexes via an unprecedented mechanism that involves hydrogen bonding between PdO(H) and H–CF3. Considering that palladium is one of the few metals that can promote aryl-CF3 bond formation, the work “will likely lead to further developments in the area of aromatic trifluoromethylation,” the researchers write.

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