Intramolecular construction of trifluoromethyl group by the palladium-catalyzed reaction of 2,3,3-trifluoroallylic carbonates with O-nucleophiles |
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Authors: | Yuji Hoshino Kazuki Isa Taisyun Hanakawa Hiroaki Tsuji Motoi Kawatsura |
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Institution: | Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo, 156-8550, Japan |
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Abstract: | The synthesis of the trifluoromethyl group containing enol ethers by the palladium-catalyzed intermolecular reaction of 2,3,3-trifluoroallylic carbonates with oxygen nucleophiles was accomplished. The reaction proceeds through the intermolecular attack of oxygen nucleophiles on the C-2 carbon atom of the allylic unit, and the intramolecular fluorine atom shift from the C-2 position to the C-3 position. The reactions with several types of alcohols and phenols proceeded smoothly, and afforded the corresponding trifluoromethyl group containing enol ethers in good to high yields. |
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Keywords: | Palladium Fluorine Trifluoromethyl group C-F bond activation Enol ether |
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