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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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Article information


Submitted
30 Jul 2010
Accepted
22 Sep 2010
First published
23 Sep 2010

Org. Biomol. Chem., 2011,9, 600-603
Article type
Paper

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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