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Tetrafluoroethylene Is Good For More Than Just Teflon

Fluorine Chemistry: Two groups report new approaches for using the fluorinated olefin as a reagent in organic synthesis

by Stephen K. Ritter
June 1, 2015 | A version of this story appeared in Volume 93, Issue 22

Tetrafluoroethylene (TFE) has long been used as an economical feedstock for making fluorinated polymers. Researchers have also used the fluorinated olefin as a starting material in organic synthesis, but the chemistry remains relatively underdeveloped. Two research teams are now reporting reactions that broaden the scope of TFE’s use as a reagent. In one case, a team led by Masato Ohashi and Sensuke Ogoshi of Osaka University, in Japan, has used TFE in nickel-catalyzed reactions with ethylene and aldehydes to make fluorinated aldehydes and ketones and with ethylene and other alkenes to make α-olefins with fluoroalkyl chains. The reactions proceed through an unprecedented five-membered “nickelacyclic” intermediate (J. Am. Chem. Soc. 2015, DOI: 10.1021/jacs.5b03587; Organometallics 2015, DOI: 10.1021/acs.organomet.5b00218). In a second case, Yusuke Takahira and Yoshitomi Morizawa of Asahi Glass, in Yokohama, Japan, have used TFE and other fluoroolefins in ruthenium carbene-catalyzed cross-metathesis reactions with enol ethers to make ether-functionalized fluorinated olefins (J. Am. Chem. Soc. 2015, DOI: 10.1021/jacs.5b03342). The Asahi researchers believe their method of combining inexpensive fluoroolefins with a hydrocarbon counterpart will enable easy synthesis of new fluorinated building blocks for polymeric materials and medicinal chemistry.


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