A review of Mg metal-promoted CF bond activation; a reliable synthetic approach to difluorinated organic compounds |
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Authors: | Kenji Uneyama Hideki Amii |
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Institution: | Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan |
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Abstract: | The carbon-fluorine bond of a trifluoromethyl group attached to a π system can be activated by metallic magnesium in the system TMSCl-THF or DMF providing a variety of difluorinated compounds via a selective CF bond cleavage. Thus, trifluoromethyl ketones, α,β-unsaturated ketones, esters, imines, and aromatics can be transformed into the corresponding difluoroenol silyl ethers, enamines, and difluoro(trimethylsilyl)methyl aromatics in good to excellent yields, respectively. This protocol enabled us to synthesize β,β-difluoroamino acids, difluoroheterocycles, and functionalized difluoroacetates. |
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Keywords: | Carbon-fluorine activation Magnesuim Difluorinated organics |
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