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Issue 2, 2011
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Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation

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Abstract

The diketone 2-fluoro-2-(trifluoromethyl)-1-phenylhexane-1,5-dione 3 was synthesized by a Mukaiyama Michael type reaction from the corresponding tetrafluoroenol silyl ether prepared from pentafluoropropiophenone. This diketone was treated under basic conditions and was converted, depending on the stoichiometry of the base, into the surprisingly stable ketol 4-fluoro-4-(trifluoromethyl)-3-hydroxy-3-phenylcyclohexanone 4 as a single diastereomer (catalytic KOH) or to the biphenylol 6-(trifluoromethyl)biphenyl-3-ol (excess KOH, THF) 5. Solvolysis of the trifluoromethyl group (anionic activation) occurred using excess KOH in alcohol. The corresponding cyclohexenone derivative 7, the usual product of Robinson annulation, might be prepared in good yield via mesylation of the ketol. Thus various unprecedented fluorinated cyclohexane and aromatic derivatives were achieved in a few steps from the commercially available pentafluoropropiophenone.

Graphical abstract: Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation

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Publication details

The article was received on 30 Jul 2010, accepted on 22 Sep 2010 and first published on 23 Sep 2010


Article type: Paper
DOI: 10.1039/C0OB00518E
Citation: Org. Biomol. Chem., 2011,9, 600-603
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    Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation

    F. Massicot, A. M. Iriarte, T. Brigaud, A. Lebrun and C. Portella, Org. Biomol. Chem., 2011, 9, 600
    DOI: 10.1039/C0OB00518E

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